Cyclotrimerization reactions of arynes and strained cycloalkynes

被引：33

作者：

Pena, Diego ^{[1
]}

Perez, Dolores ^{[1
]}

Guitian, Enrique ^{[1
]}

机构：

[1] Univ Santiago de Compostela, Fac Quim, Dept Quim Organ, Santiago De Compostela 15782, Spain

来源：

CHEMICAL RECORD | 2007年 / 7卷 / 06期

关键词：

arynes; cycloalkynes; cyclotrimerization; cycloaddition; palladium;

D O I：

10.1002/tcr.20132

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The use of arynes and related species as substrates in metal-catalyzed cycloaddition reactions leads to structurally interesting products. Palladium-catalyzed cyclotrimerization of arynes provides a new method for the synthesis of polycyclic aromatic hydrocarbons. For instance, the chemoselective formal [2 + 2 + 2] cocycloaddition of 2,3-triphenylynes with alkynes affords extended triphenylenes, which are good candidates to behave as liquid crystals. Cotrimerization of benzyne and electron-deficient alkenes selectively affords dihydrophenanthrenes or ortho-olefinated biaryls depending on the catalytic system employed. The use of 2,2'-bis(diphenylphosphino)-1,1'-binophythyl (BINAP)-based palladium(0) catalysts in the cocyclotrimerization of 7-methoxynaphthalyne and dimethyl acetylenedicarboxylate affords an enantiomerically enriched tetrasubstituted pentahelicene, the first example of a metal-catalyzed enantioselective reaction involving arynes. Strained cyclic alkynes can also participate in the palladium-catalyzed cyclotrimerization reactions, which again lead to structurally interesting products. (C) 2007 The Japan Chemical Journal Forum and Wiley Periodicals, Inc.

引用

页码：326 / 333

页数：8

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