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

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2003年 / 42卷 / 01期

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.

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页码：89 / 92

页数：4

相关论文

共 36 条

[11] A novel C-C bond forming reaction of aryl- and alkenylsilanols. A halogen-free Mizoroki-Heck type reaction [J].

Hirabayashi, K ;

Nishihara, Y ;

Mori, A ;

Hiyama, T .

TETRAHEDRON LETTERS, 1998, 39 (43) :7893-7896

[12] Conjugate addition of arylsilanes to unsaturated carbonyl compounds catalyzed by rhodium in air and water [J].

Huang, TS ;

Li, CJ .

CHEMICAL COMMUNICATIONS, 2001, (22) :2348-2349

[13] THE VINYLATION OF ARYL IODIDES CATALYZED BY CO, RH AND IR COMPLEXES [J].

IYER, S .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1995, 490 (1-2) :C27-C28

[14] CATALYTIC HEAD-TO-HEAD ALKYNE DIMERIZATION TO GIVE Z-ENYNES [J].

JUN, CH ;

LU, Z ;

CRABTREE, RH .

TETRAHEDRON LETTERS, 1992, 33 (47) :7119-7120

[15]

Koike T, 2002, SYNLETT, P301

[16] Rhodium-catalyzed coupling reactions of arylboronic acids to olefins in aqueous media [J].

Lautens, M ;

Roy, A ;

Fukuoka, K ;

Fagnou, K ;

Martín-Matute, B .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (22) :5358-5359

[17] Grignard-type carbonyl phenylation in water and under an air atmosphere [J].

Li, CJ ;

Meng, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (39) :9538-9539

[18]

Maitlis P. M., 1996, DALTON T, P2187

[19] Hydroxorhodium complex-catalyzed carbon-carbon bond-forming reactions of silanediols with α,β-unsaturated carbonyl compounds.: Mizoroki-Heck-type reaction vs conjugate addition [J].

Mori, A ;

Danda, Y ;

Fujii, T ;

Hirabayashi, K ;

Osakada, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (43) :10774-10775

[20] Cross-coupling reactions of hypervalent siloxane derivatives: An alternative to Stille and Suzuki couplings [J].

Mowery, ME ;

DeShong, P .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (05) :1684-1688

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