Lewis acid-promoted coupling reactions of acid chlorides with organoaluminum and organozinc reagents

被引：38

作者：

Arisawa, M ^{[1
]}

Torisawa, Y ^{[1
]}

Kawahara, M ^{[1
]}

Yamanaka, M ^{[1
]}

Nishida, A ^{[1
]}

Nakagawa, M ^{[1
]}

机构：

[1] CHIBA UNIV,FAC PHARMACEUT SCI,INAGE KU,CHIBA 263,JAPAN

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1997年 / 62卷 / 13期

关键词：

D O I：

10.1021/jo970244a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient synthesis of alpha,beta-unsaturated ketones by the reaction of acid chlorides with trialkylaluminum (1/3 mole equiv) in the presence of AlCl3 (1 mol equiv) is described. Dialkylzincs were also useful and are easier to prepare than trialkylaluminum. Reaction of RCOCl with R'AlCl2 or R-2'AlCl gave R'COR, without AlCl3, in high yield.

引用

页码：4327 / 4329

页数：3

共 23 条

[1] ARISAWA M, 1995, SYNTHESIS-STUTTGART, P1371
[2] EVANS PA, 1995, J ORG CHEM, V60, P298
[3] GRAY RA, 1984, J ORG CHEM, V49, P2288
[4] Acylation of oxazoles by the copper-mediated reaction of oxazol-2-ylzinc chloride derivatives
Harn, NK
Gramer, CJ
Anderson, BA
[J]. TETRAHEDRON LETTERS, 1995, 36 (52) : 9453 - 9456
[5] PREPARATION AND REACTIONS OF POLYFUNCTIONAL ORGANOZINC REAGENTS IN ORGANIC-SYNTHESIS
KNOCHEL, P
SINGER, RD
[J]. CHEMICAL REVIEWS, 1993, 93 (06) : 2117 - 2188
[6] Knochel P, 1991, COMPREHENSIVE ORGANI, V1, P211
[7] Larock RC., 1989, COMPREHENSIVE ORGANI, P686
[8] DIRECT NI-DEGREES MEDIATED SYNTHESIS OF KETONES FROM ACYL BROMIDES AND GRIGNARD-REAGENTS
MALANGA, C
ARONICA, LA
LARDICCI, L
[J]. TETRAHEDRON LETTERS, 1995, 36 (50) : 9185 - 9188
[9] Nagata T, 1996, CHEM PHARM BULL, V44, P451
[10] SELECTIVE CARBON-CARBON BOND FORMATION VIA TRANSITION-METAL CATALYSIS .36. PALLADIUM-CATALYZED ACYLATION OF ORGANOZINCS AND OTHER ORGANOMETALLICS AS A CONVENIENT ROUTE TO KETONES
NEGISHI, E
BAGHERI, V
CHATTERJEE, S
LUO, FT
MILLER, JA
STOLL, AT
[J]. TETRAHEDRON LETTERS, 1983, 24 (47) : 5181 - 5184

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