Rhodium-catalyzed multicomponent-coupling reactions involving a carborhodation-cross-coupling sequence

被引:93
作者
Shintani, Ryo [1 ]
Yamagami, Takafumi [1 ]
Hayashi, Tamio [1 ]
机构
[1] Kyoto Univ, Grad Sch Sci, Dept Chem, Kyoto 6068502, Japan
关键词
D O I
10.1021/ol061858h
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A rhodium-catalyzed multicomponent-coupling reaction has been developed that involves a cross-coupling with organohalides as part of the reaction sequence. Through several experiments toward mechanistic investigations, it has also been demonstrated that the reaction most likely proceeds via a carborhodation-oxidative addition-reductive elimination pathway, which clearly contrasts to the corresponding palladium-catalyzed processes.
引用
收藏
页码:4799 / 4801
页数:3
相关论文
共 27 条
[1]  
Bolm C, 2001, ANGEW CHEM INT EDIT, V40, P3285
[2]   Diastereo- and enantioselective catalytic carbometallative aldol cycloreduction: Tandem conjugate addition-aldol cyclization [J].
Cauble, DF ;
Gipson, JD ;
Krische, MJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (05) :1110-1111
[3]   A tandem Heck-carbocyclization/Suzuki-coupling approach to the stereoselective syntheses of asymmetric 3,3-(diarylmethylene)indolinones [J].
Cheung, WS ;
Patch, RJ ;
Player, MR .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (09) :3741-3744
[4]   Heck-Suzuki-Miyaura domino reactions involving ynamides.: An efficient access to 3-(Arylmethylene)isoindolinones [J].
Couty, S ;
Liégault, B ;
Meyer, C ;
Cossy, J .
ORGANIC LETTERS, 2004, 6 (15) :2511-2514
[5]   A domino sequence consisting of insertion, coupling, isomerization, and Diels-Alder steps yields highly fluorescent spirocycles [J].
D'Souza, DM ;
Rominger, F ;
Müller, TJJ .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (01) :153-158
[6]   Rhodium-catalyzed carbon-carbon bond forming reactions of organometallic compounds [J].
Fagnou, K ;
Lautens, M .
CHEMICAL REVIEWS, 2003, 103 (01) :169-196
[7]   Rhodium-catalyzed hydroarylation of alkynes with arylboronic acids: 1,4-shift of rhodium from 2-aryl-1-alkenylrhodium to 2-alkenylarylrhodium intermediate [J].
Hayashi, T ;
Inoue, K ;
Taniguchi, N ;
Ogasawara, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (40) :9918-9919
[8]   DICHLORO[1,1'-BIS(DIPHENYLPHOSPHINO)FERROCENE]PALLADIUM-(II) - AN EFFECTIVE CATALYST FOR CROSS-COUPLING OF SECONDARY AND PRIMARY ALKYL GRIGNARD AND ALKYLZINC REAGENTS WITH ORGANIC HALIDES [J].
HAYASHI, T ;
KONISHI, M ;
KOBORI, Y ;
KUMADA, M ;
HIGUCHI, T ;
HIROTSU, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (01) :158-163
[9]   Rhodium-catalyzed asymmetric 1,4-addition and its related asymmetric reactions [J].
Hayashi, T ;
Yamasaki, K .
CHEMICAL REVIEWS, 2003, 103 (08) :2829-2844
[10]   Novel Rh(I)-catalyzed reaction of arylzinc compounds with methyl halides [J].
Hossain, KM ;
Takagi, K .
CHEMISTRY LETTERS, 1999, (11) :1241-1242