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

被引：127

作者：

Araki, S ^{[1
]}

Kamei, T ^{[1
]}

Hirashita, T ^{[1
]}

Yamamura, H ^{[1
]}

Kawai, M ^{[1
]}

机构：

[1] Nagoya Inst Technol, Dept Appl Chem, Showa Ku, Nagoya, Aichi 4668555, Japan

来源：

ORGANIC LETTERS | 2000年 / 2卷 / 06期

关键词：

D O I：

10.1021/ol005610i

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A reductive transmetalation of the pi-allylpalladium(II) complexes, generated in situ from a catalytic amount of a palladium(0) complex and a variety of allylic substrates, with indium(I) salts proceeded smoothly in various solvents, providing a new route for allylindium(III) reagents.

引用

页码：847 / 849

页数：3

共 19 条

[1] A BARBIER ALLYLATION AND A REFORMATSKY REACTION OF CARBONYL-COMPOUNDS MEDIATED BY INDIUM(I) IODIDE [J].

ARAKI, S ;

ITO, H ;

KATSUMURA, N ;

BUTSUGAN, Y .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1989, 369 (03) :291-296

[2] PREPARATION AND SOME REACTIONS OF ALLYLIC INDIUM REAGENTS [J].

ARAKI, S ;

SHIMIZU, T ;

JOHAR, PS ;

JIN, SJ ;

BUTSUGAN, Y .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (07) :2538-2542

[3] Chelation-controlled regio- and stereoselective allylindation of norbornenols [J].

Araki, S ;

Kamei, T ;

Igarashi, Y ;

Hirashita, T ;

Yamamura, H ;

Kawai, M .

TETRAHEDRON LETTERS, 1999, 40 (45) :7999-8002

[4] Regioselective allylation and alkylation of electron-deficient alkenes with organogallium and organoindium reagents [J].

Araki, S ;

Horie, T ;

Kato, M ;

Hirashita, T ;

Yamamura, H ;

Kawai, M .

TETRAHEDRON LETTERS, 1999, 40 (12) :2331-2334

[5] Indium-mediated organometallic reactions in aqueous media: The nature of the allylindium intermediate [J].

Chan, TH ;

Yang, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (13) :3228-3229

[6]

CINTAS P, 1995, SYNLETT, P1087

[7] Preparation of γ-heterosubstituted allylindium and diindium reagents and their reactions with carbonyl compounds [J].

Hirashita, T ;

Kamei, T ;

Horie, T ;

Yamamura, H ;

Kawai, M ;

Araki, S .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (01) :172-177

[8] Allylation of aldehydes via Umpolung of π-allylpalladium(II) with triethylborane [J].

Kimura, M ;

Kiyama, I ;

Tomizawa, T ;

Horino, Y ;

Tanaka, S ;

Tamaru, Y .

TETRAHEDRON LETTERS, 1999, 40 (37) :6795-6798

[9] Carboindation of carbon-carbon triple bonds: Regioselective indium-mediated allylation of functionalized alkynes and transformation into halogen-substituted 1,4-dienes [J].

Klaps, E ;

Schmid, W .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (20) :7537-7546

[10] Aqueous Barbier-Grignard type reaction: Scope, mechanism, and synthetic applications [J].

Li, CJ .

TETRAHEDRON, 1996, 52 (16) :5643-5668

← 1 2 →