Additive effects in palladium-indium mediated Barbier type allylations

被引：22

作者：

Cleghorn, LAT

Cooper, IR

Grigg, R ^{[1
]}

MacLachlan, WS

Sridharan, V

机构：

[1] Univ Leeds, Dept Chem, Mol Innovat Divers & Automat Synth MIDAS Ctr, Leeds LS2 9JT, W Yorkshire, England

[2] GlaxoSmithKlin, Harlow CM19 5AAW, Essex, England

来源：

TETRAHEDRON LETTERS | 2003年 / 44卷 / 43期

基金：

英国工程与自然科学研究理事会;

关键词：

indium; Barbier allylation; additives;

D O I：

10.1016/j.tetlet.2003.08.103

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The effect of adding 1 equiv. of an amine or 0,2 equiv. of CuI to a Pd/In bimetallic cascade reaction is described. In the class 1 cascade reaction of aldehydes, aryl iodides and allene, generating homoallylic alcohols, the reaction time is reduced from 16 to 2 h and is accompanied by an impressive increase in yield. (C) 2003 Published by Elsevier Ltd.

引用

收藏

页码：7969 / 7973

页数：5

相关论文

共 10 条

[1] Copper(I)-promoted palladium-catalyzed cross-coupling of unsaturated tri-n-butylstannane with heteroaromatic thioether [J].

Alphonse, FA ;

Suzenet, F ;

Keromnes, A ;

Lebret, B ;

Guillaumet, G .

ORGANIC LETTERS, 2003, 5 (06) :803-805

[2] Palladium-indium mediated Barbier-type allylation of aldehydes with allenes [J].

Anwar, U ;

Grigg, R ;

Rasparini, M ;

Savic, V ;

Sridharan, V .

CHEMICAL COMMUNICATIONS, 2000, (08) :645-646

[3] Palladium catalysed cyclisation-Barbier-type allylation cascades [J].

Anwar, U ;

Grigg, R ;

Sridharan, V .

CHEMICAL COMMUNICATIONS, 2000, (11) :933-934

[4] A new preparative method for allylic indium(III) reagents by reductive transmetalation of π-allylpalladium(II) with indium(I) salts [J].

Araki, S ;

Kamei, T ;

Hirashita, T ;

Yamamura, H ;

Kawai, M .

ORGANIC LETTERS, 2000, 2 (06) :847-849

[5] INDIUM IN ORGANIC-SYNTHESIS - INDIUM-MEDIATED ALLYLATION OF CARBONYL-COMPOUNDS [J].

ARAKI, S ;

ITO, H ;

BUTSUGAN, Y .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (08) :1831-1833

[6] Barbier-type allylation of iminium ions generated in situ in aqueous medium [J].

Estevam, IHS ;

Bieber, LW .

TETRAHEDRON LETTERS, 2003, 44 (04) :667-670

[7] ON THE NATURE OF THE COPPER EFFECT IN THE STILLE CROSS-COUPLING [J].

FARINA, V ;

KAPADIA, S ;

KRISHNAN, B ;

WANG, CJ ;

LIEBESKIND, LS .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (20) :5905-5911

[8] Preparation of chiral allenylmetal reagents from enantioenriched allenyl iodides and propargylic mesylates. A comparison of indium, bismuth, and tin derivatives [J].

Marshall, JA ;

Grant, CM .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (22) :8214-8219

[9] OPTIMIZED STILLE COUPLING REACTIONS CATALYZED BY PALLADIUM ON CARBON WITH CUI AS COCATALYST [J].

ROTH, GP ;

FARINA, V ;

LIEBESKIND, LS ;

PENACABRERA, E .

TETRAHEDRON LETTERS, 1995, 36 (13) :2191-2194

[10] SELECTIVE REACTIONS USING ALLYLIC METALS [J].

YAMAMOTO, Y ;

ASAO, N .

CHEMICAL REVIEWS, 1993, 93 (06) :2207-2293