Palladium-catalyzed selective 2,3-diarylation of α,α-disubstituted 3-thiophenemethanols via cleavage of C-H and C-C bonds

被引:59
作者
Nakano, Masaya [1 ]
Satoh, Tetsuya [1 ]
Miura, Masahiro [1 ]
机构
[1] Osaka Univ, Fac Engn, Dept Appl Chem, Suita, Osaka 5650871, Japan
关键词
D O I
10.1021/jo061412e
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
alpha, alpha-Disubstituted 3-thiophenemethanols undergo selective diarylation accompanied by cleavage of the C-H and C-C bonds of the 2- and 3-positions, respectively, upon treatment with aryl bromides in the presence of a palladium catalyst to give the corresponding 2,3-diarylthiophenes in good yields.
引用
收藏
页码:8309 / 8311
页数:3
相关论文
共 38 条
[1]   Catalytic multistep reactions via palladacycles [J].
Catellani, M .
SYNLETT, 2003, (03) :298-313
[2]   THE ORGANOMETALLIC CHEMISTRY OF ALKANES [J].
CRABTREE, RH .
CHEMICAL REVIEWS, 1985, 85 (04) :245-269
[3]  
De Meijere A., 2004, Metal-Catalyzed Cross-Coupling Reactions
[4]  
Dyker G, 1999, ANGEW CHEM INT EDIT, V38, P1699, DOI 10.1002/(SICI)1521-3773(19990614)38:12<1698::AID-ANIE1698>3.0.CO
[5]  
2-6
[6]   Aryl-aryl bond formation one century after the discovery of the Ullmann reaction [J].
Hassan, J ;
Sévignon, M ;
Gozzi, C ;
Schulz, E ;
Lemaire, M .
CHEMICAL REVIEWS, 2002, 102 (05) :1359-1469
[7]  
Jun CH, 2002, CHEM-EUR J, V8, P2423, DOI 10.1002/1521-3765(20020603)8:11<2422::AID-CHEM2422>3.0.CO
[8]  
2-B
[9]   Catalytic methods for C-H bond functionalization: Application in organic synthesis [J].
Kakiuchi, F ;
Chatani, N .
ADVANCED SYNTHESIS & CATALYSIS, 2003, 345 (9-10) :1077-1101
[10]   Catalytic C-H/olefin coupling [J].
Kakiuchi, F ;
Murai, S .
ACCOUNTS OF CHEMICAL RESEARCH, 2002, 35 (10) :826-834