Iridium-catalyzed Mizoroki-Heck-type reaction of organosilicon reagents

被引:59
作者
Koike, T [1 ]
Du, XL [1 ]
Sanada, T [1 ]
Danda, Y [1 ]
Mori, A [1 ]
机构
[1] Tokyo Inst Technol, Chem Resources Lab, Yokohama, Kanagawa 2268503, Japan
关键词
alkoxysilanes; C-C coupling; homogeneous catalysis; iridium; silicon;
D O I
10.1002/anie.200390061
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Independent of substrate and solvent, the C-C bond-forming reaction of organosilicon reagents with α,β-unsaturated carbonyl compounds can be catalyzed by an iridium complex to give exclusively the Mizoroki-Heck-type addition/elimination product (see scheme). This result sharply contrasts the analogous reaction with a rhodium catalyst under similar conditions in which the 1,4-addition product is obtained preferentially. cod=cycloocta-1,5-diene.
引用
收藏
页码:89 / 92
页数:4
相关论文
共 36 条
[1]   CONVERSION OF ALKENES TO ENOL SILYL ETHERS OF ACYLSILANES BY IRIDIUM CATALYZED REACTION WITH A HYDROSILANE AND CARBON-MONOXIDE [J].
CHATANI, N ;
IKEDA, S ;
OHE, K ;
MURAI, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (24) :9710-9711
[2]   PALLADIUM-CATALYZED CROSS-COUPLING OF ARYL AND ALKENYL BORONIC ACIDS WITH ALKENES VIA OXIDATIVE ADDITION OF A CARBON-BORON BOND TO PALLADIUM(0) [J].
CHO, CS ;
UEMURA, S .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1994, 465 (1-2) :85-92
[3]  
DU X, 2002, 81 ANN M CHEM SOC JA
[4]   Mizoroki-heck type reaction of organoboron reagents with alkenes and alkynes.: A Pd(II)-catalyzed pathway with Cu(OAc)2 as an oxidant [J].
Du, XL ;
Suguro, M ;
Hirabayashi, K ;
Mori, A ;
Nishikata, T ;
Hagiwara, N ;
Kawata, K ;
Okeda, T ;
Wang, HF ;
Fugami, K ;
Kosugi, M .
ORGANIC LETTERS, 2001, 3 (21) :3313-3316
[5]  
FARRINGTON BEJ, 2002, ANGEW CHEM, V114, P169
[6]  
Farrington EJ, 2002, ANGEW CHEM INT EDIT, V41, P169, DOI 10.1002/1521-3773(20020104)41:1<169::AID-ANIE169>3.0.CO
[7]  
2-S
[8]  
Fugami K, 1998, SYNLETT, P477
[9]  
Hirabayashi K, 1999, SYNLETT, P99
[10]   Novel carbon-carbon bond formation through Mizoroki-Heck type reaction of silanols and organotin compounds [J].
Hirabayashi, K ;
Ando, J ;
Kawashima, J ;
Nishihara, Y ;
Mori, A ;
Hiyama, T .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2000, 73 (06) :1409-1417