gistfile1.txt

<?xml version="1.0" encoding="UTF-8"?><cml xmlns="http://www.chemaxon.com" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" xsi:schemaLocation="http://www.chemaxon.com/marvin/help/formats/schema/mrvSchema_6_2_0.xsd" version="ChemAxon file format v6.2, generated by v6.3.0">
<MDocument><MChemicalStruct><reaction><arrow type="DEFAULT" x1="-7.259480881745031" y1="1.3737404197296181" x2="-1.0587105901089497" y2="1.3539927419708107"></arrow><propertyList><property dictRef="NAME" title="NAME"><scalar><![CDATA[Suzuki coupling]]></scalar></property><property dictRef="EXPLAIN_REACTIVITY" title="EXPLAIN_REACTIVITY"><scalar><![CDATA[First reactant is boronic acid, boronic ester, borane, trifluoroborate salt or boronic acid anhydride. Second reactant may be halogenide or organosulfonate or methyl sulfide as these compounds behave as pseudohalogen compounds.]]></scalar></property><property dictRef="EXPLAIN_EXCLUDE" title="EXPLAIN_EXCLUDE"><scalar><![CDATA[Second reactant may not contain such functional groups which compete with the boron containing group in the transmetallation step of the catalytic cycle.]]></scalar></property><property dictRef="EXPLAIN_SELECTIVITY" title="EXPLAIN_SELECTIVITY"><scalar><![CDATA[The most negative carbon atom reacts in oxidative addition from the second molecule.]]></scalar></property><property dictRef="TOLERANCE" title="TOLERANCE"><scalar>0.005</scalar></property><property dictRef="EXPLAIN_TOLERANCE" title="EXPLAIN_TOLERANCE"><scalar></scalar></property><property dictRef="REACTIVITY" title="REACTIVITY"><scalar><![CDATA[(match(ratom(3), "[H]O[B;v3X3:1]O[H]", 1) or match(ratom(3), "[#6]O[B;v3X3:1]O[#6]", 1) or match(ratom(3), "[H][B;v3X3:1]([H])", 1) or match(ratom(3), "[B;v4X4-:1](F)(F)F", 1) or match(ratom(3), "B1OBO[B;v3X3:1]O1", 1)) and (match(ratom(4), "[#6]S([#8:1])(=O)=O", 1) or match(ratom(2), "[H]C([H])([H])[S;v2][#6:1]", 1) or match(ratom(4), "[Cl,Br,I]"))]]></scalar></property><property dictRef="SELECTIVITY" title="SELECTIVITY"><scalar>-charge(ratom(2))</scalar></property><property dictRef="EXAMPLE" title="EXAMPLE"><scalar><![CDATA[<?xml version="1.0"?><cml version="ChemAxon file format v5.9.0, generated by v5.9.0">
<MDocument><MChemicalStruct><reaction><arrow type="DEFAULT" x1="-1.2100000381469727" y1="0.550000011920929" x2="3.081409948774121" y2="0.5500000119209284"></arrow><reactantList><molecule molID="m1"><atomArray atomID="a1 a2 a3 a4 a5 a6 a7 a8 a9" elementType="C C C C C C O B O" x2="-12.828395609140179 -12.828395609140179 -11.494716487312141 -10.161037365484107 -10.161037365484107 -11.494716487312145 -10.161037365484114 -11.494716487312148 -12.828395609140186" y2="0.50263888888889 2.04263888888889 2.8126388888888894 2.042638888888889 0.5026388888888891 -0.2673611111111111 -2.577361111111114 -1.807361111111111 -2.5773611111111077"></atomArray><bondArray><bond atomRefs2="a2 a1" order="1"></bond><bond atomRefs2="a6 a1" order="2"></bond><bond atomRefs2="a3 a2" order="2"></bond><bond atomRefs2="a4 a3" order="1"></bond><bond atomRefs2="a5 a4" order="2"></bond><bond atomRefs2="a6 a5" order="1"></bond><bond atomRefs2="a8 a6" order="1"></bond><bond atomRefs2="a8 a7" order="1"></bond><bond atomRefs2="a9 a8" order="1"></bond></bondArray></molecule><molecule molID="m2"><atomArray atomID="a1 a2 a3 a4 a5 a6 a7 a8" elementType="C Br C C C C C C" x2="-5.7473582436560715 -7.081037365484107 -5.7473582436560715 -4.413679121828035 -3.08 -3.08 -4.413679121828037 -4.41367912182804" y2="-0.502638888888888 1.807361111111112 1.037361111111112 1.8073611111111116 1.0373611111111112 -0.5026388888888889 -1.2726388888888889 -2.8126388888888894"></atomArray><bondArray><bond atomRefs2="a3 a1" order="1"></bond><bond atomRefs2="a7 a1" order="2"></bond><bond atomRefs2="a3 a2" order="1"></bond><bond atomRefs2="a4 a3" order="2"></bond><bond atomRefs2="a5 a4" order="1"></bond><bond atomRefs2="a6 a5" order="2"></bond><bond atomRefs2="a7 a6" order="1"></bond><bond atomRefs2="a8 a7" order="1"></bond></bondArray></molecule></reactantList><productList><molecule molID="m3"><atomArray atomID="a1 a2 a3 a4 a5 a6 a7 a8 a9 a10 a11 a12 a13" elementType="C C C C C C C C C C C C C" x2="5.953679121828034 4.619999999999999 4.62 5.953679121828036 7.2873582436560715 7.2873582436560715 8.621037365484106 8.621037365484106 9.954716487312144 11.288395609140178 11.288395609140178 9.95471648731214 9.954716487312137" y2="0.3850000000000001 1.1550000000000011 2.695000000000001 3.4650000000000007 2.6950000000000003 1.1550000000000007 -1.1549999999999994 0.38500000000000056 1.1550000000000002 0.3849999999999997 -1.1550000000000002 -1.9250000000000005 -3.4650000000000007"></atomArray><bondArray><bond atomRefs2="a2 a1" order="1"></bond><bond atomRefs2="a6 a1" order="2"></bond><bond atomRefs2="a3 a2" order="2"></bond><bond atomRefs2="a4 a3" order="1"></bond><bond atomRefs2="a5 a4" order="2"></bond><bond atomRefs2="a6 a5" order="1"></bond><bond atomRefs2="a8 a6" order="1"></bond><bond atomRefs2="a8 a7" order="1"></bond><bond atomRefs2="a12 a7" order="2"></bond><bond atomRefs2="a9 a8" order="2"></bond><bond atomRefs2="a10 a9" order="1"></bond><bond atomRefs2="a11 a10" order="2"></bond><bond atomRefs2="a12 a11" order="1"></bond><bond atomRefs2="a13 a12" order="1"></bond></bondArray></molecule></productList></reaction></MChemicalStruct></MDocument>
<MDocument><MChemicalStruct><reaction><arrow type="DEFAULT" x1="-1.5950000286102295" y1="0.7149999737739563" x2="3.0250000953674316" y2="0.7149999737739563"></arrow><reactantList><molecule molID="m4"><atomArray atomID="a1 a2 a3 a4 a5 a6 a7 a8 a9 a10 a11" elementType="C C C C C C C O B O C" x2="-14.40896702981228 -14.40896702981228 -13.075287907984244 -11.741608786156208 -11.741608786156208 -13.075287907984245 -11.741608786156219 -11.741608786156215 -13.075287907984249 -14.408967029812286 -14.40896702981229" y2="1.1631239609013304 2.7031239609013307 3.4731239609013302 2.70312396090133 1.1631239609013295 0.3931239609013294 -3.456876039098673 -1.9168760390986732 -1.1468760390986705 -1.916876039098667 -3.456876039098667"></atomArray><bondArray><bond atomRefs2="a2 a1" order="1"></bond><bond atomRefs2="a6 a1" order="2"></bond><bond atomRefs2="a3 a2" order="2"></bond><bond atomRefs2="a4 a3" order="1"></bond><bond atomRefs2="a5 a4" order="2"></bond><bond atomRefs2="a6 a5" order="1"></bond><bond atomRefs2="a9 a6" order="1"></bond><bond atomRefs2="a8 a7" order="1"></bond><bond atomRefs2="a9 a8" order="1"></bond><bond atomRefs2="a10 a9" order="1"></bond><bond atomRefs2="a11 a10" order="1"></bond></bondArray></molecule><molecule molID="m5"><atomArray atomID="a1 a2 a3 a4 a5 a6 a7 a8 a9 a10 a11 a12 a13 a14 a15 a16 a17" elementType="C O O C C C O O O S C C C C C C C" x2="-8.661608786156208 -7.7564194976257985 -5.045906291193843 -6.291792462531262 -6.291792462531262 -7.756419497625798 -8.232305668963216 -8.34628756640576 -6.057401503935387 -7.201844535170573 -5.616808438922703 -6.647269572715347 -6.17138340137793 -4.665036096247871 -3.6345749624552255 -4.1104611337926436 -3.08" y2="3.3787695370387376 4.624655708376157 5.053958825569147 4.1487695370387385 2.608769537038738 2.132883365701319 0.6682563306067822 -1.5066478344210468 0.5542744331642385 -0.4761867006284041 -4.229699798193314 -3.085256766958129 -1.62062973186359 -1.3004457280042387 -2.4448887592394244 -3.9095157943339616 -5.053958825569147"></atomArray><bondArray><bond atomRefs2="a2 a1" order="1"></bond><bond atomRefs2="a6 a1" order="1"></bond><bond atomRefs2="a4 a2" order="1"></bond><bond atomRefs2="a4 a3" order="2"></bond><bond atomRefs2="a5 a4" order="1"></bond><bond atomRefs2="a6 a5" order="2"></bond><bond atomRefs2="a7 a6" order="1"></bond><bond atomRefs2="a10 a7" order="1"></bond><bond atomRefs2="a10 a8" order="2"></bond><bond atomRefs2="a10 a9" order="2"></bond><bond atomRefs2="a13 a10" order="1"></bond><bond atomRefs2="a12 a11" order="1"></bond><bond atomRefs2="a16 a11" order="2"></bond><bond atomRefs2="a13 a12" order="2"></bond><bond atomRefs2="a14 a13" order="1"></bond><bond atomRefs2="a15 a14" order="2"></bond><bond atomRefs2="a16 a15" order="1"></bond><bond atomRefs2="a17 a16" order="1"></bond></bondArray></molecule></reactantList><productList><molecule molID="m6"><atomArray atomID="a1 a2 a3 a4 a5 a6 a7 a8 a9 a10 a11 a12" elementType="C C C C C C C C C O C O" x2="5.095886171337418 4.62 5.650461133792643 7.156808438922703 7.632694610260122 6.602233476467481 6.172930359274492 7.0781196478049 8.542746682899436 8.542746682899436 7.078119647804901 6.602233476467482" y2="1.5660701751967687 3.030697210291306 4.175140241526493 3.8549562376671425 2.3903292025726053 1.2458861713374183 -1.4646270350945372 -0.218740863757118 -0.6946270350945369 -2.2346270350945368 -2.7105132064319557 -4.175140241526493"></atomArray><bondArray><bond atomRefs2="a2 a1" order="1"></bond><bond atomRefs2="a6 a1" order="2"></bond><bond atomRefs2="a3 a2" order="2"></bond><bond atomRefs2="a4 a3" order="1"></bond><bond atomRefs2="a5 a4" order="2"></bond><bond atomRefs2="a6 a5" order="1"></bond><bond atomRefs2="a8 a6" order="1"></bond><bond atomRefs2="a8 a7" order="2"></bond><bond atomRefs2="a11 a7" order="1"></bond><bond atomRefs2="a9 a8" order="1"></bond><bond atomRefs2="a10 a9" order="1"></bond><bond atomRefs2="a11 a10" order="1"></bond><bond atomRefs2="a12 a11" order="2"></bond></bondArray></molecule></productList></reaction></MChemicalStruct></MDocument>
<MDocument><MChemicalStruct><reaction><arrow type="DEFAULT" x1="-1.1555170312526952" y1="0.31082324027074004" x2="2.6915275829397247" y2="0.2991522896570486"></arrow><reactantList><molecule molID="m7"><atomArray atomID="a1 a2 a3 a4 a5 a6" elementType="F B F F C C" formalCharge="0 -1 0 0 0 0" x2="-12.828395609140179 -11.494716487312143 -12.264716487312143 -10.724716487312143 -10.161037365484107 -8.827358243656072" y2="-0.4399999999999996 0.33000000000000024 1.6636791218280358 -1.0036791218280352 1.1 0.32999999999999957"></atomArray><bondArray><bond atomRefs2="a1 a2" order="1"></bond><bond atomRefs2="a2 a3" order="1"></bond><bond atomRefs2="a2 a4" order="1"></bond><bond atomRefs2="a2 a5" order="1"></bond><bond atomRefs2="a5 a6" order="2"></bond></bondArray></molecule><molecule molID="m8"><atomArray atomID="a1 a2 a3 a4 a5 a6 a7" elementType="Br C C C C C C" x2="-4.413679121828041 -4.413679121828038 -3.08 -3.08 -4.413679121828036 -5.7473582436560715 -5.747358243656072" y2="-2.3100000000000005 -0.7700000000000004 -1.6653345369377348E-16 1.54 2.3100000000000005 1.540000000000001 7.216449660063518E-16"></atomArray><bondArray><bond atomRefs2="a1 a2" order="1"></bond><bond atomRefs2="a2 a3" order="1"></bond><bond atomRefs2="a3 a4" order="2"></bond><bond atomRefs2="a4 a5" order="1"></bond><bond atomRefs2="a5 a6" order="2"></bond><bond atomRefs2="a6 a7" order="1"></bond><bond atomRefs2="a2 a7" order="2"></bond></bondArray></molecule></reactantList><productList><molecule molID="m9"><atomArray atomID="a1 a2 a3 a4 a5 a6 a7 a8" elementType="C C C C C C C C" x2="7.287358243656065 5.953679121828031 5.953679121828035 7.287358243656072 7.287358243656072 5.953679121828037 4.620000000000001 4.62" y2="-2.6950000000000016 -1.924999999999999 -0.3849999999999988 0.3850000000000014 1.9250000000000014 2.6950000000000016 1.9250000000000023 0.3850000000000023"></atomArray><bondArray><bond atomRefs2="a1 a2" order="2"></bond><bond atomRefs2="a2 a3" order="1"></bond><bond atomRefs2="a3 a4" order="1"></bond><bond atomRefs2="a4 a5" order="2"></bond><bond atomRefs2="a5 a6" order="1"></bond><bond atomRefs2="a6 a7" order="2"></bond><bond atomRefs2="a7 a8" order="1"></bond><bond atomRefs2="a3 a8" order="2"></bond></bondArray></molecule></productList></reaction></MChemicalStruct></MDocument>
<MDocument><MChemicalStruct><reaction absStereo="true"><arrow type="DEFAULT" x1="-1.1356162635058702" y1="0.6365876870744213" x2="2.7565929772830877" y2="0.7296471898001554"></arrow><reactantList><molecule molID="m10" absStereo="true"><atomArray atomID="a1 a2 a3 a4 a5 a6 a7 a8 a9 a10 a11 a12 a13 a14 a15 a16 a17 a18 a19 a20 a21 a22 a23 a24 a25 a26 a27 a28 a29 a30 a31 a32 a33 a34 a35 a36 a37 a38 a39 a40 a41 a42" elementType="C C C C Si C C O C C O Si C C C C C C C O Si C C C C C C C C C C B O O O Si C C C C C C" x2="-20.830470340108388 -22.370470340108387 -22.370470340108387 -22.37047034010839 -23.91047034010839 -23.91047034010839 -23.91047034010839 -25.45047034010839 -26.22047034010839 -27.760470340108387 -28.530470340108387 -27.760470340108387 -26.42679121828035 -29.09414946193642 -26.990470340108384 -25.65679121828035 -28.32414946193642 -26.22047034010838 -28.53047034010839 -27.76047034010839 -28.53047034010839 -29.864149461936428 -27.196791218280357 -29.300470340108394 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<MDocument><MChemicalStruct><reaction><arrow type="DEFAULT" x1="-3.9049999713897705" y1="2.309999942779541" x2="1.4852805001164682" y2="2.309999942779541"></arrow><propertyList><property dictRef="REFERENCE" title="REFERENCE"><scalar><![CDATA[Tetrahedron, 2004, 60, 3813\\u20133818.]]>]]&gt;<![CDATA[</scalar></property><property dictRef="SciFinder LINK" title="SciFinder LINK"><scalar><![CDATA[https://scifinder.cas.org/scifinder/view/link_v1/reference.html?l=BmxxGlm8wGrIJ9Q6lNFFFJ1y0TW0JVu6D95wTEL3MyllSdj3c2Hneg]]>]]&gt;<![CDATA[</scalar></property></propertyList><reactantList><molecule molID="m13"><atomArray atomID="a1 a2 a3 a4 a5 a6 a7" elementType="C C C C B O O" x2="-24.749998807907104 -23.41631968607907 -22.082640564251037 -20.748961442423 -19.41528232059496 -18.081603198766928 -19.41528232059496" y2="2.0899999141693115 2.859999914169311 2.0899999141693115 2.859999914169312 2.089999914169312 2.8599999141693124 0.5499999141693119"></atomArray><bondArray><bond atomRefs2="a1 a2" order="1"></bond><bond atomRefs2="a2 a3" order="1"></bond><bond atomRefs2="a3 a4" order="1"></bond><bond atomRefs2="a4 a5" order="1"></bond><bond atomRefs2="a5 a6" order="1"></bond><bond atomRefs2="a5 a7" order="1"></bond></bondArray></molecule><molecule molID="m14"><atomArray atomID="a1 a2 a3 a4 a5 a6 a7 a8 a9 a10" elementType="C C C C C C Br C C O" x2="-8.421822922875624 -9.961822922751388 -10.731839863310427 -9.961856803993701 -8.42185680411794 -7.6518398635589016 -6.111839863589964 -12.271839863279368 -13.041848333574418 -13.041831392953252" y2="3.588708461275842 3.5886888999314683 2.254980436194465 0.9212915338018366 0.9213110951462085 2.2550195588832116 2.2550097782110257 2.254990216866652 0.9213159854016082 3.5886742290038827"></atomArray><bondArray><bond atomRefs2="a1 a2" order="1"></bond><bond atomRefs2="a1 a6" order="2"></bond><bond atomRefs2="a2 a3" order="2"></bond><bond atomRefs2="a3 a4" order="1"></bond><bond atomRefs2="a3 a8" order="1"></bond><bond atomRefs2="a4 a5" order="2"></bond><bond atomRefs2="a5 a6" order="1"></bond><bond atomRefs2="a6 a7" order="1"></bond><bond atomRefs2="a8 a9" order="1"></bond><bond atomRefs2="a8 a10" order="2"></bond></bondArray></molecule></reactantList><productList><molecule molID="m15"><atomArray atomID="a1 a2 a3 a4 a5 a6 a7 a8 a9 a10 a11 a12 a13" elementType="C C C C C C C C C C C C O" x2="8.570481556211867 7.030481556336102 6.2604646157770585 7.030447675093784 8.570447674969548 9.340464615528589 10.88046461549753 11.65047308579258 13.190473085761521 13.960481556056571 4.720464615808119 3.9504561455130682 3.9504730861342265" y2="3.444885747247156 3.444866185902784 2.111157722165782 0.7774688197731507 0.777488381117523 2.1111968448545255 2.1111870641823405 3.444861295647385 3.4448515149751993 4.778525746440243 2.1111675028379677 0.7774932713729237 3.4448515149751993"></atomArray><bondArray><bond atomRefs2="a1 a2" order="1"></bond><bond atomRefs2="a2 a3" order="2"></bond><bond atomRefs2="a3 a4" order="1"></bond><bond atomRefs2="a4 a5" order="2"></bond><bond atomRefs2="a5 a6" order="1"></bond><bond atomRefs2="a1 a6" order="2"></bond><bond atomRefs2="a6 a7" order="1"></bond><bond atomRefs2="a7 a8" order="1"></bond><bond atomRefs2="a8 a9" order="1"></bond><bond atomRefs2="a9 a10" order="1"></bond><bond atomRefs2="a3 a11" order="1"></bond><bond atomRefs2="a11 a12" order="1"></bond><bond atomRefs2="a11 a13" order="2"></bond></bondArray></molecule></productList></reaction></MChemicalStruct></MDocument>
<MDocument><MChemicalStruct><reaction><arrow type="DEFAULT" x1="-3.519999921321869" y1="6.159999847412109" x2="1.8702805501843698" y2="6.159999847412109"></arrow><propertyList><property dictRef="REFERENCE" title="REFERENCE"><scalar><![CDATA[Tetrahedron, 2004, 60, 3813\\u20133818.]]>]]&gt;<![CDATA[</scalar></property><property dictRef="SciFinder LINK" title="SciFinder LINK"><scalar><![CDATA[https://scifinder.cas.org/scifinder/view/link_v1/reference.html?l=BmxxGlm8wGrIJ9Q6lNFFFJ1y0TW0JVu6D95wTEL3MyllSdj3c2Hneg]]>]]&gt;<![CDATA[</scalar></property></propertyList><reactantList><molecule molID="m16"><atomArray atomID="a1 a2 a3 a4 a5 a6 a7" elementType="C C C C B O O" x2="-25.355002880096436 -24.0213237582684 -22.687644636440368 -21.35396551461233 -20.020286392784293 -18.68660727095626 -20.020286392784293" y2="6.050000190734863 6.820000190734863 6.050000190734863 6.820000190734864 6.050000190734863 6.820000190734865 4.510000190734864"></atomArray><bondArray><bond atomRefs2="a1 a2" order="1"></bond><bond atomRefs2="a2 a3" order="1"></bond><bond atomRefs2="a3 a4" order="1"></bond><bond atomRefs2="a4 a5" order="1"></bond><bond atomRefs2="a5 a6" order="1"></bond><bond atomRefs2="a5 a7" order="1"></bond></bondArray></molecule><molecule molID="m17"><atomArray atomID="a1 a2 a3 a4 a5 a6 a7 a8 a9 a10 a11 a12 a13 a14 a15" elementType="C C C C C C C C C C C C C C Br" x2="-11.440000295639038 -12.773640295639037 -14.107434295639038 -14.107434295639038 -12.773640295639037 -11.440000295639038 -10.106360295639039 -8.772566295639038 -8.772566295639038 -10.106360295639039 -7.438867612896999 -6.10516893015496 -6.10516893015496 -7.438867612896999 -10.106398793998974" y2="6.600000281333923 7.370000281333923 6.600000281333923 5.060000281333924 4.290000281333923 5.060000281333924 4.290000281333923 5.060000281333924 6.600000281333923 7.370000281333923 4.289966399843138 5.059932518352352 6.599932518352352 7.369966399843138 8.910000280852714"></atomArray><bondArray><bond atomRefs2="a1 a2" order="2"></bond><bond atomRefs2="a2 a3" order="1"></bond><bond atomRefs2="a3 a4" order="2"></bond><bond atomRefs2="a4 a5" order="1"></bond><bond atomRefs2="a5 a6" order="2"></bond><bond atomRefs2="a7 a8" order="2"></bond><bond atomRefs2="a9 a10" order="2"></bond><bond atomRefs2="a1 a6" order="1"></bond><bond atomRefs2="a1 a10" order="1"></bond><bond atomRefs2="a6 a7" order="1"></bond><bond atomRefs2="a9 a14" order="1"></bond><bond atomRefs2="a8 a9" order="1"></bond><bond atomRefs2="a8 a11" order="1"></bond><bond atomRefs2="a11 a12" order="2"></bond><bond atomRefs2="a12 a13" order="1"></bond><bond atomRefs2="a13 a14" order="2"></bond><bond atomRefs2="a10 a15" order="1"></bond></bondArray></molecule></reactantList><productList><molecule molID="m18"><atomArray atomID="a1 a2 a3 a4 a5 a6 a7 a8 a9 a10 a11 a12 a13 a14 a15 a16 a17 a18" elementType="C C C C C C C C C C C C C C C C C C" x2="6.930000066757202 5.596360066757202 4.262566066757202 4.262566066757202 5.596360066757202 6.930000066757202 8.263640066757201 9.597434066757202 9.597434066757202 8.263640066757201 10.931132749499243 12.264831432241284 12.264831432241284 10.931132749499243 8.263601568397268 9.597261440628598 9.597222942268665 10.930902064096701" y2="5.169999618530273 5.9399996185302735 5.169999618530273 3.6299996185302734 2.8599996185302734 3.6299996185302734 2.8599996185302734 3.6299996185302734 5.169999618530273 5.9399996185302735 2.8599657370394875 3.629931855548702 5.169931855548702 5.939965737039488 7.479999618049065 8.250032958366166 9.790032957884957 10.560032957884959"></atomArray><bondArray><bond atomRefs2="a1 a2" order="2"></bond><bond atomRefs2="a2 a3" order="1"></bond><bond atomRefs2="a3 a4" order="2"></bond><bond atomRefs2="a4 a5" order="1"></bond><bond atomRefs2="a5 a6" order="2"></bond><bond atomRefs2="a7 a8" order="2"></bond><bond atomRefs2="a9 a10" order="2"></bond><bond atomRefs2="a1 a6" order="1"></bond><bond atomRefs2="a1 a10" order="1"></bond><bond atomRefs2="a6 a7" order="1"></bond><bond atomRefs2="a9 a14" order="1"></bond><bond atomRefs2="a8 a9" order="1"></bond><bond atomRefs2="a8 a11" order="1"></bond><bond atomRefs2="a11 a12" order="2"></bond><bond atomRefs2="a12 a13" order="1"></bond><bond atomRefs2="a13 a14" order="2"></bond><bond atomRefs2="a10 a15" order="1"></bond><bond atomRefs2="a15 a16" order="1"></bond><bond atomRefs2="a16 a17" order="1"></bond><bond atomRefs2="a17 a18" order="1"></bond></bondArray></molecule></productList></reaction></MChemicalStruct></MDocument>
<MDocument><MChemicalStruct><reaction><arrow type="DEFAULT" x1="-3.7399999499320984" y1="4.510000228881836" x2="1.6502805215741403" y2="4.510000228881836"></arrow><propertyList><property dictRef="REFERENCE" title="REFERENCE"><scalar><![CDATA[Tetrahedron, 2004, 60, 3813\\u20133818.]]>]]&gt;<![CDATA[</scalar></property><property dictRef="SciFinder LINK" title="SciFinder LINK"><scalar><![CDATA[https://scifinder.cas.org/scifinder/view/link_v1/reference.html?l=BmxxGlm8wGrIJ9Q6lNFFFJ1y0TW0JVu6D95wTEL3MyllSdj3c2Hneg]]>]]&gt;<![CDATA[</scalar></property></propertyList><reactantList><molecule molID="m19"><atomArray atomID="a1 a2 a3 a4 a5 a6 a7" elementType="C C C C B O O" x2="-22.65999674797058 -21.326317626142547 -19.992638504314513 -18.658959382486476 -17.325280260658438 -15.991601138830404 -17.325280260658438" y2="4.564999938011169 5.334999938011169 4.564999938011169 5.33499993801117 4.564999938011169 5.334999938011171 3.02499993801117"></atomArray><bondArray><bond atomRefs2="a1 a2" order="1"></bond><bond atomRefs2="a2 a3" order="1"></bond><bond atomRefs2="a3 a4" order="1"></bond><bond atomRefs2="a4 a5" order="1"></bond><bond atomRefs2="a5 a6" order="1"></bond><bond atomRefs2="a5 a7" order="1"></bond></bondArray></molecule><molecule molID="m20"><atomArray atomID="a1 a2 a3 a4 a5 a6 a7 a8 a9 a10 a11" elementType="C C C C C C N C C C Br" x2="-9.569999694824219 -10.903639694824218 -12.237433694824219 -12.237433694824219 -10.903639694824218 -9.569999694824219 -8.23635969482422 -6.902565694824219 -6.902565694824219 -8.23635969482422 -5.568900932071948" y2="4.950000305175781 5.720000305175781 4.950000305175781 3.4100003051757812 2.640000305175781 3.4100003051757812 2.640000305175781 3.4100003051757812 4.950000305175781 5.720000305175781 5.72002517528903"></atomArray><bondArray><bond atomRefs2="a1 a2" order="1"></bond><bond atomRefs2="a2 a3" order="2"></bond><bond atomRefs2="a3 a4" order="1"></bond><bond atomRefs2="a4 a5" order="2"></bond><bond atomRefs2="a5 a6" order="1"></bond><bond atomRefs2="a7 a8" order="2"></bond><bond atomRefs2="a8 a9" order="1"></bond><bond atomRefs2="a9 a10" order="2"></bond><bond atomRefs2="a1 a6" order="2"></bond><bond atomRefs2="a1 a10" order="1"></bond><bond atomRefs2="a6 a7" order="1"></bond><bond atomRefs2="a9 a11" order="1"></bond></bondArray></molecule></reactantList><productList><molecule molID="m21"><atomArray atomID="a1 a2 a3 a4 a5 a6 a7 a8 a9 a10 a11 a12 a13 a14" elementType="C C C C C C N C C C C C C C" x2="6.215000152587891 4.881360152587891 3.5475661525878905 3.5475661525878905 4.881360152587891 6.215000152587891 7.548640152587891 8.88243415258789 8.88243415258789 7.548640152587891 10.216098915340163 10.216070197652414 11.549734960404686 11.549706242716937" y2="2.914999861717224 3.684999861717224 2.914999861717224 1.374999861717224 0.6049998617172241 1.374999861717224 0.6049998617172241 1.374999861717224 2.914999861717224 3.684999861717224 3.685024731830473 5.225024731562711 5.99504960167596 7.535049601408198"></atomArray><bondArray><bond atomRefs2="a1 a2" order="1"></bond><bond atomRefs2="a2 a3" order="2"></bond><bond atomRefs2="a3 a4" order="1"></bond><bond atomRefs2="a4 a5" order="2"></bond><bond atomRefs2="a5 a6" order="1"></bond><bond atomRefs2="a7 a8" order="2"></bond><bond atomRefs2="a8 a9" order="1"></bond><bond atomRefs2="a9 a10" order="2"></bond><bond atomRefs2="a1 a6" order="2"></bond><bond atomRefs2="a1 a10" order="1"></bond><bond atomRefs2="a6 a7" order="1"></bond><bond atomRefs2="a9 a11" order="1"></bond><bond atomRefs2="a11 a12" order="1"></bond><bond atomRefs2="a12 a13" order="1"></bond><bond atomRefs2="a13 a14" order="1"></bond></bondArray></molecule></productList></reaction></MChemicalStruct></MDocument>
<MDocument><MChemicalStruct><reaction><arrow type="DEFAULT" x1="-3.7949999570846558" y1="4.400000095367432" x2="1.595280514421583" y2="4.400000095367432"></arrow><propertyList><property dictRef="REFERENCE" title="REFERENCE"><scalar><![CDATA[Tetrahedron, 2004, 60, 3813\\u20133818.]]>]]&gt;<![CDATA[</scalar></property><property dictRef="SciFinder LINK" title="SciFinder LINK"><scalar><![CDATA[https://scifinder.cas.org/scifinder/view/link_v1/reference.html?l=BmxxGlm8wGrIJ9Q6lNFFFJ1y0TW0JVu6D95wTEL3MyllSdj3c2Hneg]]>]]&gt;<![CDATA[</scalar></property></propertyList><reactantList><molecule molID="m22"><atomArray atomID="a1 a2 a3 a4 a5 a6 a7" elementType="C C C C B O O" x2="-21.120001554489136 -19.786322432661102 -18.452643310833068 -17.11896418900503 -15.785285067176993 -14.451605945348959 -15.785285067176993" y2="4.674999713897705 5.444999713897705 4.674999713897705 5.4449997138977055 4.674999713897705 5.444999713897706 3.1349997138977055"></atomArray><bondArray><bond atomRefs2="a1 a2" order="1"></bond><bond atomRefs2="a2 a3" order="1"></bond><bond atomRefs2="a3 a4" order="1"></bond><bond atomRefs2="a4 a5" order="1"></bond><bond atomRefs2="a5 a6" order="1"></bond><bond atomRefs2="a5 a7" order="1"></bond></bondArray></molecule><molecule molID="m23"><atomArray atomID="a1 a2 a3 a4 a5 a6 a7 a8 a9 a10 a11" elementType="C C C C C C C C C C Br" x2="-9.020000457763672 -10.353640457763671 -11.687434457763672 -11.687434457763672 -10.353640457763671 -9.020000457763672 -7.686360457763673 -6.352566457763672 -6.352566457763672 -7.686360457763673 -7.686360457763673" y2="4.729999799728393 5.499999799728394 4.729999799728393 3.1899997997283935 2.4199997997283935 3.1899997997283935 2.4199997997283935 3.1899997997283935 4.729999799728393 5.499999799728394 7.039999799728394"></atomArray><bondArray><bond atomRefs2="a1 a2" order="1"></bond><bond atomRefs2="a2 a3" order="2"></bond><bond atomRefs2="a3 a4" order="1"></bond><bond atomRefs2="a4 a5" order="2"></bond><bond atomRefs2="a5 a6" order="1"></bond><bond atomRefs2="a7 a8" order="2"></bond><bond atomRefs2="a8 a9" order="1"></bond><bond atomRefs2="a9 a10" order="2"></bond><bond atomRefs2="a1 a6" order="2"></bond><bond atomRefs2="a1 a10" order="1"></bond><bond atomRefs2="a6 a7" order="1"></bond><bond atomRefs2="a10 a11" order="1"></bond></bondArray></molecule></reactantList><productList><molecule molID="m24"><atomArray atomID="a1 a2 a3 a4 a5 a6 a7 a8 a9 a10 a11 a12 a13 a14" elementType="C C C C C C C C C C C C C C" x2="6.215000152587891 4.881360152587891 3.5475661525878905 3.5475661525878905 4.881360152587891 6.215000152587891 7.548640152587891 8.88243415258789 8.88243415258789 7.548640152587891 7.548601654227957 8.882261526459287 8.882223028099354 10.215882900330683" y2="2.914999861717224 3.684999861717224 2.914999861717224 1.374999861717224 0.6049998617172241 1.374999861717224 0.6049998617172241 1.374999861717224 2.914999861717224 3.684999861717224 5.224999861236015 5.995033201553118 7.535033201071909 8.30506654138901"></atomArray><bondArray><bond atomRefs2="a1 a2" order="1"></bond><bond atomRefs2="a1 a6" order="2"></bond><bond atomRefs2="a1 a10" order="1"></bond><bond atomRefs2="a2 a3" order="2"></bond><bond atomRefs2="a3 a4" order="1"></bond><bond atomRefs2="a4 a5" order="2"></bond><bond atomRefs2="a5 a6" order="1"></bond><bond atomRefs2="a6 a7" order="1"></bond><bond atomRefs2="a7 a8" order="2"></bond><bond atomRefs2="a8 a9" order="1"></bond><bond atomRefs2="a9 a10" order="2"></bond><bond atomRefs2="a10 a11" order="1"></bond><bond atomRefs2="a11 a12" order="1"></bond><bond atomRefs2="a12 a13" order="1"></bond><bond atomRefs2="a13 a14" order="1"></bond></bondArray></molecule></productList></reaction></MChemicalStruct></MDocument>
<MDocument><MChemicalStruct><reaction><arrow type="DEFAULT" x1="-13.31000018119812" y1="5.28000020980835" x2="-7.919719709691881" y2="5.28000020980835"></arrow><propertyList><property dictRef="REFERENCE" title="REFERENCE"><scalar><![CDATA[Tetrahedron, 2004, 60, 3813\\u20133818.]]>]]&gt;<![CDATA[</scalar></property><property dictRef="SciFinder LINK" title="SciFinder LINK"><scalar><![CDATA[https://scifinder.cas.org/scifinder/view/link_v1/reference.html?l=BmxxGlm8wGrIJ9Q6lNFFFJ1y0TW0JVu6D95wTEL3MyllSdj3c2Hneg]]>]]&gt;<![CDATA[</scalar></property></propertyList><reactantList><molecule molID="m25"><atomArray atomID="a1 a2 a3 a4 a5 a6 a7 a8 a9 a10 a11" elementType="C C C C B O O C C C C" x2="-34.70499873161316 -33.371319609785125 -32.03764048795709 -30.703961366129054 -29.370282244301016 -28.036603122472982 -29.370282244301016 -36.03867785344119 -37.37235697526923 -38.70603609709727 -40.0397152189253" y2="5.390000224113464 6.160000224113464 5.390000224113464 6.160000224113465 5.390000224113464 6.160000224113466 3.8500002241134648 6.160000224113464 5.3900002241134635 6.160000224113463 5.3900002241134635"></atomArray><bondArray><bond atomRefs2="a1 a2" order="1"></bond><bond atomRefs2="a2 a3" order="1"></bond><bond atomRefs2="a3 a4" order="1"></bond><bond atomRefs2="a4 a5" order="1"></bond><bond atomRefs2="a5 a6" order="1"></bond><bond atomRefs2="a5 a7" order="1"></bond><bond atomRefs2="a1 a8" order="1"></bond><bond atomRefs2="a8 a9" order="1"></bond><bond atomRefs2="a9 a10" order="1"></bond><bond atomRefs2="a10 a11" order="1"></bond></bondArray></molecule><molecule molID="m26"><atomArray atomID="a1 a2 a3 a4 a5 a6 a7 a8 a9" elementType="C C C C C C Br C N" x2="-16.866630527785333 -17.63664746834438 -19.176681349462463 -19.946698290021498 -19.176681349462463 -17.636647468344375 -15.326630527785337 -21.4866982900215 -23.026698290021496" y2="5.316663302641206 6.650332643689466 6.650332643689464 5.3166633026412065 3.9829939615929515 3.9829939615929497 5.316663302641205 5.316663302641206 5.316663302641204"></atomArray><bondArray><bond atomRefs2="a1 a2" order="1"></bond><bond atomRefs2="a2 a3" order="2"></bond><bond atomRefs2="a3 a4" order="1"></bond><bond atomRefs2="a4 a5" order="2"></bond><bond atomRefs2="a5 a6" order="1"></bond><bond atomRefs2="a1 a6" order="2"></bond><bond atomRefs2="a1 a7" order="1"></bond><bond atomRefs2="a4 a8" order="1"></bond><bond atomRefs2="a8 a9" order="3"></bond></bondArray></molecule></reactantList><productList><molecule molID="m27"><atomArray atomID="a1 a2 a3 a4 a5 a6 a7 a8 a9 a10 a11 a12 a13 a14 a15 a16" elementType="C C C C C C C C C C C C C C C N" x2="-0.2965660583397751 -1.8365660582155394 -2.60658299877458 -1.836599939457856 -0.29659993958209085 0.4734170009769487 2.01341700094589 2.78342547124094 4.32342547120988 5.093433941504931 6.6334339414738706 7.4034424117689195 8.943442411737863 9.71345088203291 -4.146582998743521 -5.686582998743521" y2="4.461909542387617 4.461889981043245 3.1281815173062433 1.7944926149136124 1.7945121762579848 3.1282206399949875 3.128210859322801 4.461885090787846 4.461875310115661 5.795549541580707 5.795539760908519 7.129213992373564 7.129204211701379 8.462878443166424 3.1281912979784297 3.128191297978428"></atomArray><bondArray><bond atomRefs2="a1 a2" order="1"></bond><bond atomRefs2="a2 a3" order="2"></bond><bond atomRefs2="a3 a4" order="1"></bond><bond atomRefs2="a4 a5" order="2"></bond><bond atomRefs2="a5 a6" order="1"></bond><bond atomRefs2="a1 a6" order="2"></bond><bond atomRefs2="a6 a7" order="1"></bond><bond atomRefs2="a7 a8" order="1"></bond><bond atomRefs2="a8 a9" order="1"></bond><bond atomRefs2="a9 a10" order="1"></bond><bond atomRefs2="a10 a11" order="1"></bond><bond atomRefs2="a11 a12" order="1"></bond><bond atomRefs2="a12 a13" order="1"></bond><bond atomRefs2="a13 a14" order="1"></bond><bond atomRefs2="a3 a15" order="1"></bond><bond atomRefs2="a15 a16" order="3"></bond></bondArray></molecule></productList></reaction></MChemicalStruct></MDocument>
<MDocument><MChemicalStruct><reaction><arrow type="DEFAULT" x1="-13.31000018119812" y1="5.28000020980835" x2="-7.919719709691881" y2="5.28000020980835"></arrow><propertyList><property dictRef="REFERENCE" title="REFERENCE"><scalar><![CDATA[Tetrahedron, 2004, 60, 3813\\u20133818.]]>]]&gt;<![CDATA[</scalar></property><property dictRef="SciFinder LINK" title="SciFinder LINK"><scalar><![CDATA[https://scifinder.cas.org/scifinder/view/link_v1/reference.html?l=BmxxGlm8wGrIJ9Q6lNFFFJ1y0TW0JVu6D95wTEL3MyllSdj3c2Hneg]]>]]&gt;<![CDATA[</scalar></property></propertyList><reactantList><molecule molID="m28"><atomArray atomID="a1 a2 a3 a4 a5 a6 a7 a8 a9 a10 a11" elementType="C C C C B O O C C C C" x2="-34.70499873161316 -33.371319609785125 -32.03764048795709 -30.703961366129054 -29.370282244301016 -28.036603122472982 -29.370282244301016 -36.03867785344119 -37.37235697526923 -38.70603609709727 -40.0397152189253" y2="5.390000224113464 6.160000224113464 5.390000224113464 6.160000224113465 5.390000224113464 6.160000224113466 3.8500002241134648 6.160000224113464 5.3900002241134635 6.160000224113463 5.3900002241134635"></atomArray><bondArray><bond atomRefs2="a1 a2" order="1"></bond><bond atomRefs2="a2 a3" order="1"></bond><bond atomRefs2="a3 a4" order="1"></bond><bond atomRefs2="a4 a5" order="1"></bond><bond atomRefs2="a5 a6" order="1"></bond><bond atomRefs2="a5 a7" order="1"></bond><bond atomRefs2="a1 a8" order="1"></bond><bond atomRefs2="a8 a9" order="1"></bond><bond atomRefs2="a9 a10" order="1"></bond><bond atomRefs2="a10 a11" order="1"></bond></bondArray></molecule><molecule molID="m29"><atomArray atomID="a1 a2 a3 a4 a5 a6 a7 a8 a9 a10" elementType="C C C C C C Br C C C" x2="-17.36163136701873 -18.131648307577777 -19.67168218869586 -20.441699129254896 -19.67168218869586 -18.131648307577773 -15.821631367018735 -17.36165677790389 -17.361656777903885 -21.981699129254896" y2="5.426662959318452 6.760332300366712 6.76033230036671 5.4266629593184526 4.092993618270198 4.092993618270196 5.426662959318451 8.094016312503944 2.759309606132964 5.426662959318452"></atomArray><bondArray><bond atomRefs2="a1 a2" order="1"></bond><bond atomRefs2="a2 a3" order="2"></bond><bond atomRefs2="a3 a4" order="1"></bond><bond atomRefs2="a4 a5" order="2"></bond><bond atomRefs2="a5 a6" order="1"></bond><bond atomRefs2="a1 a6" order="2"></bond><bond atomRefs2="a1 a7" order="1"></bond><bond atomRefs2="a2 a8" order="1"></bond><bond atomRefs2="a6 a9" order="1"></bond><bond atomRefs2="a4 a10" order="1"></bond></bondArray></molecule></reactantList><productList><molecule molID="m30"><atomArray atomID="a1 a2 a3 a4 a5 a6 a7 a8 a9 a10 a11 a12 a13 a14 a15 a16 a17" elementType="C C C C C C C C C C C C C C C C C" x2="-0.9565660324117546 -2.496566032287519 -3.2665829728465594 -2.4965999135298356 -0.9565999136540704 -0.1865829730950308 1.3534170268739105 2.1234254971689603 3.6634254971379008 4.4334339674329515 5.973433967401891 6.74344243769694 8.283442437665883 9.053450907960931 -4.806582972815501 -0.18656603241175485 -0.18659144335901978" y2="5.066909561461103 5.066890000116731 3.7331815363797296 2.3994926339870988 2.399512195331471 3.733220659068474 3.7332108783962874 5.066885109861333 5.0668753291891475 6.400549560654193 6.400539779982005 7.73421401144705 7.734204230774865 9.06787846223991 3.733191317051916 6.400588683289139 1.065837963866427"></atomArray><bondArray><bond atomRefs2="a1 a2" order="1"></bond><bond atomRefs2="a2 a3" order="2"></bond><bond atomRefs2="a3 a4" order="1"></bond><bond atomRefs2="a4 a5" order="2"></bond><bond atomRefs2="a5 a6" order="1"></bond><bond atomRefs2="a1 a6" order="2"></bond><bond atomRefs2="a6 a7" order="1"></bond><bond atomRefs2="a7 a8" order="1"></bond><bond atomRefs2="a8 a9" order="1"></bond><bond atomRefs2="a9 a10" order="1"></bond><bond atomRefs2="a10 a11" order="1"></bond><bond atomRefs2="a11 a12" order="1"></bond><bond atomRefs2="a12 a13" order="1"></bond><bond atomRefs2="a13 a14" order="1"></bond><bond atomRefs2="a3 a15" order="1"></bond><bond atomRefs2="a1 a16" order="1"></bond><bond atomRefs2="a5 a17" order="1"></bond></bondArray></molecule></productList></reaction></MChemicalStruct></MDocument>
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]]></scalar></property><property dictRef="EXCLUDE" title="EXCLUDE"><scalar><![CDATA[match(reactant(1), "[B,Zn,Mg,Al,Sn]")]]></scalar></property><property dictRef="DESCRIPTION" title="DESCRIPTION"><scalar><![CDATA[Suzuki is a C-C bond forming palladium-catalysed cross-coupling reaction between organoboron compounds (boranes, boronic acids, boronate esters or trifluoroborates) and halides or pseudohalides.]]></scalar></property><property dictRef="PREPARATION" title="PREPARATION"><scalar><![CDATA[Stirring 1.2-1.5 eq. organoboron compound with 1 eq. halide(pseudohalide) 0.01-5 mol% Pd with 2x amount of coordinating ligand and 2 eq. base in protic solvent or aprotic solvent-water mixture under Ar for 0.1-72 hours at room temperature or higher temperature (refluxing solvent).]]></scalar></property><property dictRef="SOLVENT" title="SOLVENT"><scalar><![CDATA[alcohols 
glymes
aprotic solvents (eg. toluene, THF, dioxane) mixed with 5-20% water]]></scalar></property><property dictRef="TEMPERATURE / Celsius degree" title="TEMPERATURE / Celsius degree"><scalar>25-130</scalar></property><property dictRef="MEDIA" title="MEDIA"><scalar><![CDATA[basic
inert atmosphere]]></scalar></property><property dictRef="REACTION TIME / h" title="REACTION TIME / h"><scalar>0.1-72</scalar></property><property dictRef="TOTAL TIME / h" title="TOTAL TIME / h"><scalar>4-76</scalar></property><property dictRef="YIELD / %" title="YIELD / %"><scalar>20-90</scalar></property><property dictRef="GENERALITY" title="GENERALITY"><scalar>3</scalar></property><property dictRef="DIFFICULTY" title="DIFFICULTY"><scalar>3</scalar></property><property dictRef="REPRODUCABILITY" title="REPRODUCABILITY"><scalar>3</scalar></property><property dictRef="SAFETY" title="SAFETY"><scalar>1</scalar></property><property dictRef="ENVIRONMENTAL HAZARD" title="ENVIRONMENTAL HAZARD"><scalar>1</scalar></property><property dictRef="REFERENCES" title="REFERENCES"><scalar><![CDATA[A. Suzuki, Tetrahedron Lett., 1979, 20, 3437.
A. Suzuki, Tetrahedron Lett., 1981, 22, 127.
A. Suzuki, Tetrahedron, 1983, 39, 8271.
A. Suzuki, J. Am. Chem. Soc., 1985, 107, 972.
A. Suzuki, J. Am. Chem. Soc., 1987, 109, 4756.
A. Suzuki, Pur Appl. Chem., 1991, 63, 419.
N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457 (Review).
A. Suzuki, in Metal-Catalyzed Cross-Coupling Reactions; 1998, F. Diederich, P.J. Stang, eds.; Wiley-VCH Verlag GmbH: Weinheim, Germany, pp 49-97 (Review).
S.P. Stanforth, Tetrahedron, 1998, 54, 263 (Review).
J.J. Li, Alcaloids: Chem. Biol. Perspect., 1999, 14, 437 (Review).
H. Groger, J. Pract. Chem., 2000, 342, 334.
R. Franzen, Can. J. Chem., 2000, 78, 957.
C.R. LeBlond, A.T. Andrews, Y. Sun, J.R. Sowa Jr., Org. Lett., 2001, 3, 1557.
P.N. Collier, A.D. Champbell, I. Patel, T.M. Raynham, R.J.K. Taylor, J. Org. Chem., 2002, 67, 1802.
Y. Urawa, K. Ogura, Tetrahedron Lett., 2003, 44, 271.
W.-J. Liu, Y.-X. Xie, Y. Liang, J.-H. Li, Synthesis, 2006, 860-864
J.H. Kirchoff, M.R. Netherton, I.D. Hill, G.C. Fu, J. Am. Chem. Soc., 2002, 124, 13662-13663
K.L. Billingsley, K.W. Anderson, S.L. Buchwald, Angew. Chem. Int. Ed., 2006, 45, 3484-3488
M.J. Martinelli, P.J. Reider, Org. Lett., 2006, 8, 1787-1789
J. Baxter, D. Steinhuebel, M. Palucki, I.W. Davies, Org. Lett., 2005, 7, 215-218
J. Wu, Q. Zhu, L. Wang, R. Fathi, Z. Yang, J. Org. Chem., 2003, 68, 670-673
M. Shimizu, C. Nakamaki, K. Shimono, M. Shelper, T. Kurahashi, T. Hiyama, J. Am. Chem. Soc., 2005, 127, 12506-12507
G.A. Molander, C.R. Bernardi, J. Org. Chem., 2002, 67, 8424-8429.
Organic Letters, 2008, 10, 1333-1336.
Tetrahedron, 2004, 60, 3813\u20133818.
Journal of Organic Chemistry, 2008, 73, 7803-7806.
Organic Letters, 2009, 11, 2121-2124.]]></scalar></property><property dictRef="AUTHOR" title="AUTHOR"><scalar><![CDATA[J. Varga
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Application of coordinating ligand (like triphenylphosphine) to help the solvatation of Pd(0). Recent catalysts ligands and method developments help avoiding beta elimination side reactions.]]></scalar></property><property dictRef="SUBTYPE" title="SUBTYPE"><scalar><![CDATA[oxidative addition, transmetallation, reductive elimination]]></scalar></property><property dictRef="TYPE" title="TYPE"><scalar><![CDATA[addition, elimination]]></scalar></property></propertyList><reactantList><molecule molID="m1"><atomArray atomID="a1 a2" elementType="C B" mrvMap="1 3" x2="-20.649999618530273 -19.109999618530274" y2="1.4583333730697632 1.4583333730697632"></atomArray><bondArray><bond id="b1" atomRefs2="a1 a2" order="1"></bond></bondArray></molecule><molecule molID="m2"><atomArray atomID="a1 a2" elementType="O C" mrvMap="4 2" mrvQueryProps="L,O,S,Cl,Br,I: 0" x2="-11.899999618530273 -10.359999618530274" y2="1.3416666984558105 1.3416666984558105"></atomArray><bondArray><bond id="b1" atomRefs2="a1 a2" order="1"></bond></bondArray></molecule></reactantList><productList><molecule molID="m3"><atomArray atomID="a1 a2" elementType="C C" mrvMap="1 2" x2="2.0416667461395264 3.5816667461395264" y2="1.3416666984558105 1.3416666984558105"></atomArray><bondArray><bond id="b1" atomRefs2="a1 a2" order="1"></bond></bondArray></molecule></productList></reaction></MChemicalStruct></MDocument>
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