Stereospecific Stille-coupling reaction of (Z)-1,2-bis(trimethylstannyl)ethenes with hypervalent iodonium salts

被引：20

作者：

Kang, SK

Lee, YT

Lee, SH

机构：

[1] Sungkyunkwan Univ, Dept Chem, Suwon 440746, South Korea

[2] Sungkyunkwan Univ, Res Inst Basic Sci, Suwon 440746, South Korea

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 18期

关键词：

palladium and compounds; hypervalent element; tin and compounds; Stille coupling; regioselection; stereoselection;

D O I：

10.1016/S0040-4039(99)00575-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The Stille coupling of (Z)-1,2-bis(trimethylstannyl)ethenes with hypervalent iodonium salts (1 equiv) proceeded stereospecifically in the presence of PdCl2 (5 mol %) in DMF at room temperature to afford partially substituted (Z)-vinylstannanes under mild conditions. Alternatively, the use of 2 equivalents of hypervalent iodonium salts afforded tri-substituted alkenes. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

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收藏

页码：3573 / 3576

页数：4

相关论文

共 14 条

[1] SYNTHESIS AND CHARACTERIZATION OF ALKYL-SUBSTITUTED POLY[E-1,2-(2,2'-DITHIENYL)ETHYLENE]S [J].

CATELLANI, M ;

LUZZATI, S ;

MUSCO, A ;

SPERONI, F .

SYNTHETIC METALS, 1994, 62 (03) :223-228

[2] SYNTHESIS OF (+/-)-BENZOLEUKOTRIENE-B3 - A NOVEL LEUKOTRIENE-B4 ANALOG [J].

DJURIC, SW ;

HAACK, RA ;

YU, SS .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1989, (11) :2133-2134

[3] New perspectives in the cross-coupling reactions of organostannanes [J].

Farina, V .

PURE AND APPLIED CHEMISTRY, 1996, 68 (01) :73-78

[4]

FARINA V, 1995, COMPREHENSIVE ORGANO, V12, P200

[5] PALLADIUM(0) CATALYZED COUPLING OF TRANS-1,2-BIS(TRI-N-BUTYLSTANNYL)ETHYLENE WITH AROMATIC HALIDES - A CONVENIENT SYNTHESIS OF SUBSTITUTED TRANS-BETA-BROMOSTYRENES [J].

HAACK, RA ;

PENNING, TD ;

DJURIC, SW ;

DZIUBA, JA .

TETRAHEDRON LETTERS, 1988, 29 (23) :2783-2786

[6] Palladium-catalyzed coupling of organostannanes with hypervalent iodonium salts [J].

Kang, SK ;

Lee, HW ;

Jang, SB ;

Kim, TH ;

Kim, JS .

SYNTHETIC COMMUNICATIONS, 1996, 26 (23) :4311-4318

[7] Palladium-catalyzed cross-coupling of organostannanes with iodanes [J].

Kang, SK ;

Lee, HW ;

Kim, JS ;

Choi, SC .

TETRAHEDRON LETTERS, 1996, 37 (21) :3723-3726

[8] PALLADIUM CATALYSIS IN ORGANOTIN CHEMISTRY - ADDITION OF HEXAALKYLDITINS TO ALKYNES [J].

MITCHELL, TN ;

AMAMRIA, A ;

KILLING, H ;

RUTSCHOW, D .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1986, 304 (1-2) :257-265

[9]

MITCHELL TN, 1992, SYNTHESIS-STUTTGART, P803

[10] SOME CHEMISTRY OF ORGANOTIN SYNTHONS CONTAINING 2 ORGANOTIN MOIETIES [J].

MITCHELL, TN ;

KWETKAT, K ;

RUTSCHOW, D ;

SCHNEIDER, U .

TETRAHEDRON, 1989, 45 (04) :969-978