Pd-Catalyzed β-Selective Direct C-H Bond Arylation of Thiophenes with Aryltrimethylsilanes

被引:89
作者
Funaki, Kenji [1 ]
Sato, Tetsuo [1 ,2 ]
Oi, Shuichi [1 ,2 ]
机构
[1] Tohoku Univ, Grad Sch Engn, Dept Appl Chem, Aoba Ku, Sendai, Miyagi 9808579, Japan
[2] Tohoku Univ, Environm Conservat Res Inst, Aoba Ku, Sendai, Miyagi 9808579, Japan
关键词
CROSS-COUPLING REACTIONS; ARYL HALIDES; DERIVATIVES; SILICON;
D O I
10.1021/ol3029109
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Direct arylation of thiophenes and benzothiophenes with aryltrimethylsilanes was effectively catalyzed by PdCl2(MeCN)(2) in the presence of CuCl2 as an oxidant. The reaction preferentially occurred at the beta-position of both thiophenes and benzothiophenes.
引用
收藏
页码:6186 / 6189
页数:4
相关论文
共 35 条
[1]   Aryl-aryl bond formation by transition-metal-catalyzed direct arylation [J].
Alberico, Dino ;
Scott, Mark E. ;
Lautens, Mark .
CHEMICAL REVIEWS, 2007, 107 (01) :174-238
[2]  
[Anonymous], 2008, ORGANOMETALLICS
[3]   Gold-Catalyzed Direct Arylation [J].
Ball, Liam T. ;
Lloyd-Jones, Guy C. ;
Russell, Christopher A. .
SCIENCE, 2012, 337 (6102) :1644-1648
[4]   Regiocontrolled synthesis of 1,2-diaryl-1H-imidazoles by palladium- and copper-mediated direct coupling of 1-aryl-1H-imidazoles with aryl halides under ligandless conditions [J].
Bellina, F ;
Cauteruccio, S ;
Mannina, L ;
Rossi, R ;
Viel, S .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (03) :693-703
[5]  
de Meijere A., 2004, MetalCatalyzed CrossCoupling Reactions, V1
[6]   CLEAVAGES OF ARYL-SILICON AND RELATED BONDS BY ELECTROPHILES [J].
EABORN, C .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1975, 100 (01) :43-57
[7]   Palladium-catalyzed Direct C-H Bond Arylation of Simple Arenes with Aryltrimethylsilanes [J].
Funaki, Kenji ;
Kawai, Hiroshi ;
Sato, Tetsuo ;
Oi, Shuichi .
CHEMISTRY LETTERS, 2011, 40 (09) :1050-1052
[8]   Tuning the Regioselectivity of Palladium-Catalyzed Direct Arylation of Azoles by Metal Coordination [J].
Gorelsky, Serge I. .
ORGANOMETALLICS, 2012, 31 (03) :794-797
[9]   Direct thiophene arylation catalysed by Palladium [J].
Gozzi, C ;
Lavenot, L ;
Ilg, K ;
Penalva, V ;
Lemaire, M .
TETRAHEDRON LETTERS, 1997, 38 (51) :8867-8870
[10]   Iridium Catalysis for C-H Bond Arylation of Heteroarenes with lodoarenes [J].
Join, Benoit ;
Yamamoto, Takuya ;
Itami, Kenichiro .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (20) :3644-3647