PALLADIUM-CATALYZED OXIDATIVE DIMERIZATION OF STANNYLQUINONES - A SIMPLE METHOD FOR THE SYNTHESIS OF SYMMETRICAL 2,2'-BISQUINONES

被引：37

作者：

LIEBESKIND, LS

RIESINGER, SW

机构：

[1] Department of Chemistry, Emory University Atlanta

来源：

TETRAHEDRON LETTERS | 1991年 / 32卷 / 41期

关键词：

STANNYLQUINONES; BISQUINONES; STILLE CROSS-COUPLING; PALLADIUM-CATALYZED CROSS-COUPLING; OXIDATIVE DIMERIZATION;

D O I：

10.1016/S0040-4039(00)93528-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Stannylquinones, prepared by heating 4-alkynyl-4-hydroxy-2-cyclobutenones with n-Bu3SnOMe, undergo oxidative dimerization to 2,2'-bisquinones in N-methylpyrrolidone in the presence of 10% Cl2Pd(PPh3)2 and 20% CuI using a full equivalent of 1,4-benzoquinone as the stoichiometric oxidant.

引用

页码：5681 / 5682

页数：2

共 7 条

[1] SYNTHESES OF 1,3-DIENES AND 1,4-DIENES BY THE OXIDATIVE COUPLING OF 1-ALKENYLSTANNANES AND 2-ALKENYLSTANNANES IN THE PRESENCE OF PALLADIUM CATALYST
KANEMOTO, S
MATSUBARA, S
OSHIMA, K
UTIMOTO, K
NOZAKI, H
[J]. CHEMISTRY LETTERS, 1987, (01) : 5 - 6
[2] KAUFFMAN GB, 1983, INORG SYN, V22, P101
[3] STANNYLQUINONES - SYNTHESIS AND UTILIZATION AS QUINONE CARBANION SYNTHETIC EQUIVALENTS
LIEBESKIND, LS
FOSTER, BS
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (23) : 8612 - 8613
[4] 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
[5] THE PALLADIUM-CATALYZED CROSS-COUPLING REACTIONS OF ORGANOTIN REAGENTS WITH ORGANIC ELECTROPHILES
STILLE, JK
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1986, 25 (06): : 508 - 523
[6] Thomson R. H., 1987, NATURALLY OCCURRING
[7] TOLSTIKOV GA, 1989, SYNTHESIS-STUTTGART, V8, P633

← 1 →