HIGHLY VERSATILE METHODS FOR THE SYNTHESIS OF QUINONYLPORPHYRINS VIA BENZANNULATION OF FISCHER CARBENE COMPLEXES AND PALLADIUM-CATALYZED CROSS-COUPLING REACTIONS

被引：35

作者：

CHAN, CS ^{[1
]}

TSE, AKS ^{[1
]}

CHAN, KS ^{[1
]}

机构：

[1] CHINESE UNIV HONG KONG,DEPT CHEM,SHA TIN,HONG KONG

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1994年 / 59卷 / 20期

关键词：

D O I：

10.1021/jo00099a046

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Covalently-Linked porphyrin mono- and tetraquinones with well-defined distances and orientations were synthesized on the basis of two synthetic approaches. (1) The benzannulation of Fischer carbene complexes with meso-(alkynylphenyl)-substituted porphyrins, followed by oxidation, produced quinone-linked porphyrins, with both electron-donating and -withdrawing substituents on the quinone moieties. (2) The palladium-catalyzed Suzuki cross-coupling reactions of (2,5-dimethoxyphenyl)boronic acid with porphyrin meso-aryl triflates and aryl bromides, followed by subsequent demethylation and oxidation, gave meso-(benzoquinonylphenyl)-substituted porphyrins.

引用

页码：6084 / 6089

页数：6

共 40 条

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