Ruthenium-catalyzed reactions of acyclic α,β-enones with olefins and their reaction mechanisms

被引：61

作者：

Sato, T ^{[1
]}

Kakiuchi, F ^{[1
]}

Chatani, N ^{[1
]}

Murai, S ^{[1
]}

机构：

[1] Osaka Univ, Fac Engn, Dept Appl Chem, Suita, Osaka 5650871, Japan

来源：

CHEMISTRY LETTERS | 1998年 / 09期

关键词：

D O I：

10.1246/cl.1998.893

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The reaction of 4,4-dimethyl-5-phenyl-4-peneten-3-one with styrene (2) using Ru(H)(2)(CO)(PPh3)(3) as the catalyst gave the stereochemically retained product. In the case of 2,2-dimethyl-4-hexen-3-one, the stereochemically inverted branched product was obtained. These results are consistent with two different reaction pathways operating, i.e. one involving a direct C-H bond cleavage and the other, a pathway involving hydrometallation.

引用

页码：893 / 894

页数：2

共 16 条

[1]

BILLIG E, 1968, J CHEM SOC CHEM COMM, P1307

[2]

Cornils B., 1996, APPL HOMOGENEOUS CAT

[3] Transition metal-catalyzed intramolecular C-H/olefin coupling [J].

Fujii, N ;

Kakiuchi, F ;

Chatani, N ;

Murai, S .

CHEMISTRY LETTERS, 1996, (11) :939-940

[4] Transition metal-catalyzed intramolecular cyclization of 1,5- and 1,6-dienes via direct cleavage and addition of the carbon-hydrogen bond [J].

Fujii, N ;

Kakiuchi, F ;

Yamada, A ;

Chatani, N ;

Murai, S .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1998, 71 (01) :285-298

[5] Asymmetric intramolecular C-H/olefin coupling: Asymmetric cyclization reactions of 1,5-dienes catalyzed by rhodium complexes [J].

Fujii, N ;

Kakiuchi, F ;

Yamada, A ;

Chatani, N ;

Murai, S .

CHEMISTRY LETTERS, 1997, (05) :425-426

[6] STOICHIOMETRIC DIMERIZATION OF METHYL ACRYLATE MEDIATED BY PD(ACAC)2.HBF4 SYSTEMS AND ITS RELEVANCE TO THE MECHANISM OF CATALYTIC DIMERIZATION OF ACRYLATES (HACAC = MECOCH2COME) [J].

GUIBERT, I ;

NEIBECKER, D ;

TKATCHENKO, I .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (23) :1850-1852

[7] DESIGN AND STUDY OF RH(III) CATALYSTS FOR THE SELECTIVE TAIL-TO-TAIL DIMERIZATION OF METHYL ACRYLATE [J].

HAUPTMAN, E ;

SABOETIENNE, S ;

WHITE, PS ;

BROOKHART, M ;

GARNER, JM ;

FAGAN, PJ ;

CALABRESE, JC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (18) :8038-8060

[8] CATALYTIC ADDITION OF OLEFINIC C-H BONDS TO OLEFINS [J].

KAKIUCHI, F ;

TANAKA, Y ;

SATO, T ;

CHATANI, N ;

MURAI, S .

CHEMISTRY LETTERS, 1995, (08) :679-680

[9] Catalytic dimerization of acrylonitrile [J].

Kashiwagi, K ;

Sugise, R ;

Shimakawa, T ;

Matuura, T ;

Shirai, M ;

Kakiuchi, F ;

Murai, S .

ORGANOMETALLICS, 1997, 16 (11) :2233-2235

[10]

KEIM W, 1982, COMPREHENSIVE ORGANO, pCH52

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