3,5-二(4-甲基苯基)吡啶的Suzuki偶联合成及其光学性能
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摘要
以3,5-二溴吡啶和对甲基苯硼酸为原料,醋酸钯为催化剂,经Suzuki偶联反应合成了3,5-二(4-甲基苯基)吡啶(1),收率73%,其结构和性能经1H NMR,13C NMR,IR,元素分析,UV-Vis,FL和X-射线单晶衍射表征。结果表明:1(CCDC:1509844)属正交晶系,空间群P212121,晶胞参数a=6.447 8(12),b=7.240 2(14),c=29.890 0(6),β=90°。1为非平面刚性共轭分子,荧光量子产率13.9%。
3,5-Bis( 4-methylphenyl) pyridine( 1) with yield of 73% was synthesized by Suzuki crosscoupling reaction,using 3,5-bromide pyridine and 4-methylphenyl boronic acid as materials and palladium acetate as catalyst.The structures and properties were characterized by1 H NMR,13 C NMR,IR,elemental analysis,UV-Vis,FL and X-ray single crystal diffraction.The results showed that 1( CCDC: 1509844) belongs to orthorhombic system and space group P212121 with a = 6.447 8( 12),b = 7.240 2( 14) ,c = 29.890 0( 6) ,β = 90°.1 was a non-planar,rigid and conjugated molecule with photoluminescence quantum efficiency of 13.9%.
3,5-Bis( 4-methylphenyl) pyridine( 1) with yield of 73% was synthesized by Suzuki crosscoupling reaction,using 3,5-bromide pyridine and 4-methylphenyl boronic acid as materials and palladium acetate as catalyst.The structures and properties were characterized by1 H NMR,13 C NMR,IR,elemental analysis,UV-Vis,FL and X-ray single crystal diffraction.The results showed that 1( CCDC: 1509844) belongs to orthorhombic system and space group P212121 with a = 6.447 8( 12),b = 7.240 2( 14) ,c = 29.890 0( 6) ,β = 90°.1 was a non-planar,rigid and conjugated molecule with photoluminescence quantum efficiency of 13.9%.
引文
[1]Zou G F,Zhang S Q,Wang J X,et al.Asymmetric construction of functionalized 1,2-dihydropyridine and pyridine derivatives with adjacent stereocenters via a unified metal-free catalytic approach[J].Org Chem,2016,81(13):5717-5725.
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[3]张斌.二溴吡啶的选择性偶联反应和多氟苯的选择性偶联反应[D].杭州:浙江工业大学,2013.
[4]Rao M L N,Dhanorkar R J.Triarylbismuthanes as threefold aryl-transfer reagents in regioselective crosscoupling reactions with bromopyridines and quinolines[J].Eur J Org Chem,2014,2014(24):5214-5228.
[5]Zhang J,Wu Y,Zhu Z W,et al.Application of palladacycle catalyst in the synthesis of monoarylpyridyl bromides[J].Appl Organomet Chem,2007,21(11):935-940.
[6]周少林,徐利文,夏春谷,等.Suzuki偶联反应的最新研究进展[J].有机化学,2004,24(12):1501-1512.
[7]Beaumard F,Dauban P,Dodd R H.One-pot double Suzuki-Miyaura couplings:Rapid access to nonsymmetrical tri(hetero)aryl derivatives[J].Org Lett,2009,11(8):1801-1804.
[8]Dai X,Chen Y,Garrell S,et al.Ligand-dependent siteselective Suzuki cross-coupling of 3,5-dichloropyridazines[J].J Org Chem,2013,44(51):7758-7763.
[9]Guram A S,Wang X,Bunel E E,et al.New catalysts for Suzuki-Miyaura coupling reactions of heteroatomsubstituted heteroaryl chlorides J].J Org Chem,2007,72(14):5104-5112.
[10]王碧玉,倪沛钟,范吉理,等.钯催化溴代水杨醛与吡啶硼酸的Suzuki交叉偶联反应[J].有机化学,2014,(12):2471-2477.
[11]李凡超,柳林,乔洪冰,等.三联吡啶修饰的新型苯并二噻吩电子给-受体分子的合成及性能研究[J].合成化学,2016,24(5):374-379.
[2]Zhang J,Zhao L,Song M,et al.Highly efficient cyclopalladated ferrocenylimine catalyst for Suzuki crosscoupling reaction of 3-pyridylboronic pinacol ester with aryl halides[J].J Organomet Chem,2006,691(6):1301-1306.
[3]张斌.二溴吡啶的选择性偶联反应和多氟苯的选择性偶联反应[D].杭州:浙江工业大学,2013.
[4]Rao M L N,Dhanorkar R J.Triarylbismuthanes as threefold aryl-transfer reagents in regioselective crosscoupling reactions with bromopyridines and quinolines[J].Eur J Org Chem,2014,2014(24):5214-5228.
[5]Zhang J,Wu Y,Zhu Z W,et al.Application of palladacycle catalyst in the synthesis of monoarylpyridyl bromides[J].Appl Organomet Chem,2007,21(11):935-940.
[6]周少林,徐利文,夏春谷,等.Suzuki偶联反应的最新研究进展[J].有机化学,2004,24(12):1501-1512.
[7]Beaumard F,Dauban P,Dodd R H.One-pot double Suzuki-Miyaura couplings:Rapid access to nonsymmetrical tri(hetero)aryl derivatives[J].Org Lett,2009,11(8):1801-1804.
[8]Dai X,Chen Y,Garrell S,et al.Ligand-dependent siteselective Suzuki cross-coupling of 3,5-dichloropyridazines[J].J Org Chem,2013,44(51):7758-7763.
[9]Guram A S,Wang X,Bunel E E,et al.New catalysts for Suzuki-Miyaura coupling reactions of heteroatomsubstituted heteroaryl chlorides J].J Org Chem,2007,72(14):5104-5112.
[10]王碧玉,倪沛钟,范吉理,等.钯催化溴代水杨醛与吡啶硼酸的Suzuki交叉偶联反应[J].有机化学,2014,(12):2471-2477.
[11]李凡超,柳林,乔洪冰,等.三联吡啶修饰的新型苯并二噻吩电子给-受体分子的合成及性能研究[J].合成化学,2016,24(5):374-379.