Allylic Arylation of 1,3-Dienes via Hydroboration/Migrative Suzuki-Miyaura Cross-Coupling Reactions

被引:20
作者
Zhang, Xiao-Ming [1 ,2 ]
Yang, Jie [1 ,2 ]
Zhuang, Qing-Bo [1 ,2 ]
Tu, Yong-Qiang [1 ,2 ,3 ]
Chen, Zongyuan [4 ]
Shao, Hui [3 ]
Wang, Shao-Hua [1 ,2 ,5 ]
Zhang, Fu-Min [1 ,2 ]
机构
[1] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China
[2] Lanzhou Univ, Dept Chem, Lanzhou 730000, Peoples R China
[3] Shanghai Jiao Tong Univ, Sch Chem & Chem Engn, Shanghai 200240, Peoples R China
[4] Lanzhou Univ, Sch Nucl Sci & Technol, Radiochem Lab, Lanzhou 730000, Peoples R China
[5] Lanzhou Univ, Sch Pharm, Lanzhou 730000, Peoples R China
来源
ACS CATALYSIS | 2018年 / 8卷 / 07期
关键词
palladium catalysis; Suzuki-Miyaura reaction; migrative cross-coupling; allylic compounds; regioselectivity; ALKENE ISOMERIZATION-HYDROBORATION; CATALYZED BETA-ARYLATION; TERTIARY BORONIC ESTERS; CARBON BOND FORMATION; ORGANIC-SYNTHESIS; TERMINAL ALKENES; REMOTE FUNCTIONALIZATION; CONJUGATED DIENES; COBALT CATALYSTS; ARYL HALIDES;
D O I
10.1021/acscatal.8b01823
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
The hydroboration/Pd-catalyzed migrative Suzuki-Miyaura cross-coupling of 1,3-dienes with electron deficient aryl halides has been developed, which enables the synthesis of branched allylarenes directly from primary homoallylic alkyl boranes. A ligand-tuned linear- or branch-selective coupling for these aryl halides has also been achieved.
引用
收藏
页码:6094 / 6099
页数:11
相关论文
共 68 条
[1]   Palladium-Catalyzed β-Arylation of Silyl Ketene Acetals and Application to the Synthesis of Benzo-Fused δ-Lactones [J].
Aspin, Sam ;
Lopez-Suarez, Laura ;
Larini, Paolo ;
Goutierre, Anne-Sophie ;
Jazzar, Rodolphe ;
Baudoin, Olivier .
ORGANIC LETTERS, 2013, 15 (19) :5056-5059
[2]   Synthesis of Aromatic α-Aminoesters: Palladium-Catalyzed Long-Range Arylation of Primary Csp3-H Bonds [J].
Aspin, Sam ;
Goutierre, Anne-Sophie ;
Larini, Paolo ;
Jazzar, Rodolphe ;
Baudoin, Olivier .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (43) :10808-10811
[3]   Linear-Selective Hydroarylation of Unactivated Terminal and Internal Olefins with Trifluoromethyl-Substituted Arenes [J].
Bair, Joseph S. ;
Schramm, York ;
Sergeev, Alexey G. ;
Clot, Eric ;
Eisenstein, Odile ;
Hartwig, John F. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (38) :13098-13101
[4]   Bite angle effects of diphosphines in C-C and C-X bond forming cross coupling reactions [J].
Birkholz , Mandy-Nicole ;
Freixa, Zoraida ;
van Leeuwen, Piet W. N. M. .
CHEMICAL SOCIETY REVIEWS, 2009, 38 (04) :1099-1118
[5]   HYDROBORATION .49. EFFECT OF STRUCTURE ON SELECTIVE MONO-HYDROBORATION OF REPRESENTATIVE CONJUGATED DIENES BY 9-BORABICYCLO[3.3.1]NONANE [J].
BROWN, HC ;
LIOTTA, R ;
KRAMER, GW .
JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (06) :1058-1063
[6]   An Easily Accessed Nickel Nanoparticle Catalyst for Alkene Hydrosilylation with Tertiary Silanes [J].
Buslov, Ivan ;
Song, Fang ;
Hu, Xile .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (40) :12295-12299
[7]   Chemoselective Alkene Hydrosilylation Catalyzed by Nickel Pincer Complexes [J].
Buslov, Ivan ;
Becouse, Jeanne ;
Mazza, Simona ;
Montandon-Clerc, Mickael ;
Hu, Xile .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (48) :14523-14526
[8]   Enantiospecific, Regioselective Cross-Coupling Reactions of Secondary Allylic Boronic Esters [J].
Chausset-Boissarie, Laetitia ;
Ghozati, Kazem ;
LaBine, Emily ;
Chen, Jack L. -Y. ;
Aggarwal, Varinder K. ;
Crudden, Cathleen M. .
CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (52) :17698-17701
[9]  
Chemler SR, 2001, ANGEW CHEM INT EDIT, V40, P4544, DOI 10.1002/1521-3773(20011217)40:24<4544::AID-ANIE4544>3.0.CO
[10]  
2-N