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
ARAKI, S
ITO, H
KATSUMURA, N
BUTSUGAN, Y
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1989, 369 (03) : 291 - 296
[2] PREPARATION AND SOME REACTIONS OF ALLYLIC INDIUM REAGENTS
ARAKI, S
SHIMIZU, T
JOHAR, PS
JIN, SJ
BUTSUGAN, Y
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (07) : 2538 - 2542
[3] Chelation-controlled regio- and stereoselective allylindation of norbornenols
Araki, S
Kamei, T
Igarashi, Y
Hirashita, T
Yamamura, H
Kawai, M
[J]. TETRAHEDRON LETTERS, 1999, 40 (45) : 7999 - 8002
[4] Regioselective allylation and alkylation of electron-deficient alkenes with organogallium and organoindium reagents
Araki, S
Horie, T
Kato, M
Hirashita, T
Yamamura, H
Kawai, M
[J]. TETRAHEDRON LETTERS, 1999, 40 (12) : 2331 - 2334
[5] Indium-mediated organometallic reactions in aqueous media: The nature of the allylindium intermediate
Chan, TH
Yang, Y
[J]. 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
Hirashita, T
Kamei, T
Horie, T
Yamamura, H
Kawai, M
Araki, S
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (01) : 172 - 177
[8] Allylation of aldehydes via Umpolung of π-allylpalladium(II) with triethylborane
Kimura, M
Kiyama, I
Tomizawa, T
Horino, Y
Tanaka, S
Tamaru, Y
[J]. 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
Klaps, E
Schmid, W
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (20) : 7537 - 7546
[10] Aqueous Barbier-Grignard type reaction: Scope, mechanism, and synthetic applications
Li, CJ
[J]. TETRAHEDRON, 1996, 52 (16) : 5643 - 5668

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