COUPLING BETWEEN VINYL OR ARYL IODIDES AND VINYL ZINC BROMIDES(EITHER BEARING AN ALKOXY MOIETY OR TRISUBSTITUTED) UNDER PD(0) CATALYSIS

被引：18

作者：

LABAUDINIERE, L ^{[1
]}

NORMANT, JF ^{[1
]}

机构：

[1] UNIV PARIS 06,CHIM ORGANOELEMENTS LAB,CNRS,TOUR 44-45,4 PL JUSSIEU,F-75252 PARIS 05,FRANCE

来源：

TETRAHEDRON LETTERS | 1992年 / 33卷 / 41期

关键词：

VINYLATION; ARYLATION; ZINC REAGENTS; COPPER (I) SALTS;

D O I：

10.1016/S0040-4039(00)60026-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A tert-butoxy group in allylic or homoallylic position on vinyl zinc bromides does not hinder their coupling with p-iodoanisole under Pd(0) catalysis, as does a methoxy group. Furthermore, use of a polar solvent and of a stoichiometric amount of CuBr greatly enhances the reactivity of a trisubstituted vinylic zinc reagent towards vinyl or aryl iodides under Pd(0) catalysis.

引用

页码：6139 / 6142

页数：4

共 9 条

[1] THE CROSS-COUPLING REACTIONS OF ORGANIC HALIDES WITH ORGANIC DERIVATIVES OF TIN, MERCURY AND COPPER CATALYZED BY PALLADIUM
BELETSKAYA, IP
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1983, 250 (01) : 551 - 564
[2] 3-STANNYLCYCLOBUTENEDIONES AS NUCLEOPHILIC CYCLOBUTENEDIONE EQUIVALENTS - SYNTHESIS OF SUBSTITUTED CYCLOBUTENEDIONES AND CYCLOBUTENEDIONE MONOACETALS AND THE BENEFICIAL EFFECT OF CATALYTIC COPPER IODIDE ON THE STILLE REACTION
LIEBESKIND, LS
FENGL, RW
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (19) : 5359 - 5364
[3] SYNTHESIS OF SUBSTITUTED CYCLOBUTENEDIONES BY THE PALLADIUM CATALYZED CROSS-COUPLING OF HALOCYCLOBUTENEDIONES WITH ORGANOSTANNANES
LIEBESKIND, LS
WANG, JY
[J]. TETRAHEDRON LETTERS, 1990, 31 (30) : 4293 - 4296
[4] NEW STRATEGIES FOR ANNULATIONS - A HIGHLY CONVERGENT AND STEREOSELECTIVE SYNTHESIS OF AN OCTAHYDRONAPHTHALENE SYNTHON FOR DIHYDROCOMPACTIN
MARINO, JP
LONG, JK
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (23) : 7916 - 7917
[5] ALLYLMETALATIONS - THE ALLYLZINCATION OF 1-(TRIMETHYLSILYL)-1-ALKYNES
MOLANDER, GA
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (26) : 5409 - 5411
[6] NEGISHI EI, 1982, ACCOUNTS CHEM RES, P340
[7] ALLYLIC ORGANOBISMETALLIC REAGENTS .1.
NORMANT, JF
QUIRION, JC
ALEXAKIS, A
MASUDA, Y
[J]. TETRAHEDRON LETTERS, 1989, 30 (30) : 3955 - 3958
[8] PALLADIUM-CATALYZED COUPLING OF VINYL TRIFLATES WITH ORGANOSTANNANES - SYNTHETIC AND MECHANISTIC STUDIES
SCOTT, WJ
STILLE, JK
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (11) : 3033 - 3040
[9] A CONVENIENT AND EFFICIENT UNSYMMETRICAL KETONE SYNTHESIS FROM ACID-CHLORIDES AND ALKYL IODIDES CATALYZED BY PALLADIUM
TAMARU, Y
OCHIAI, H
SANDA, F
YOSHIDA, Z
[J]. TETRAHEDRON LETTERS, 1985, 26 (45) : 5529 - 5532

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