Intramolecular aryl migration from tin to carbon via a radical atom-transfer process

被引：25

作者：

Wakabayashi, K ^{[1
]}

Yorimitsu, H ^{[1
]}

Shinokubo, H ^{[1
]}

Oshima, K ^{[1
]}

机构：

[1] Kyoto Univ, Grad Sch Engn, Dept Chem Mat, Kyoto 6068501, Japan

来源：

ORGANIC LETTERS | 2000年 / 2卷 / 13期

关键词：

D O I：

10.1021/ol005971y

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Triethylborane-induced intramolecular 1,4-aryl migration from tin to a carbon-centered radical is described. Treatment of 3-iodoalkyldimethylphenylstannanes with Et3B in benzene at reflux followed by an addition of MeMgl provides 3-phenylalkyltrimethylstannanes in good yield via a radical atom-transfer process.

引用

页码：1899 / 1901

页数：3

共 33 条

[1] INTRA-MOLECULAR AROMATIC IPSO-SUBSTITUTION IN THE PHOTOLYSIS OF 2-IODOAZOBENZENES [J].

BENATI, L ;

SPAGNOLO, P ;

TUNDO, A ;

ZANARDI, G .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1979, (03) :141-143

[2] Synthesis of biaryls by intramolecular radical transfer: use of phosphinates [J].

Clive, DLJ ;

Kang, SZ .

TETRAHEDRON LETTERS, 2000, 41 (09) :1315-1319

[3] ATOM-TRANSFER CYCLIZATION - A NOVEL ISOMERIZATION OF HEX-5-YNYL IODIDES TO (IODOMETHYLENE)CYCLOPENTANES [J].

CURRAN, DP ;

CHEN, MH ;

KIM, D .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (09) :2489-2490

[4] CONTROLLING RADICAL-CHAIN REACTIONS BY UNIMOLECULAR CHAIN TRANSFER - INTRAMOLECULAR HYDROGEN-TRANSFER REACTIONS OF SILICON HYDRIDES [J].

CURRAN, DP ;

XU, JY ;

LAZZARINI, E .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (24) :6603-6604

[5] 'Giese-type' radical addition reactions to an acceptor that functions by a unimolecular chain transfer reaction of a silicon hydride [J].

Curran, DP ;

Xu, JY .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1995, (24) :3061-3063

[6]

Curran DP, 1997, SYNLETT, P1102

[7] Unimolecular chain transfer (UMCT) reactions: Concepts, preliminary results with silicon hydrides, and future potential [J].

Curran, DP ;

Xu, JY ;

Lazzarini, E .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1995, (24) :3049-3059

[8] THE DESIGN AND APPLICATION OF FREE-RADICAL CHAIN REACTIONS IN ORGANIC-SYNTHESIS .2. [J].

CURRAN, DP .

SYNTHESIS-STUTTGART, 1988, (07) :489-513

[9] Observations on the nature of the tethering chain in the synthesis of biaryls and heterobiaryls via intramolecular free radical ipso substitution reactions. [J].

daMata, MLEN ;

Motherwell, WB ;

Ujjainwalla, F .

TETRAHEDRON LETTERS, 1997, 38 (01) :141-144

[10] Steric and electronic effects in the synthesis of biaryls and their heterocyclic congeners using intramolecular free radical [1,5] ipso substitution reactions. [J].

daMata, MLEN ;

Motherwell, WB ;

Ujjainwalla, F .

TETRAHEDRON LETTERS, 1997, 38 (01) :137-140

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