Gold catalysis:: Oxepines from γ-alkynylfurans

被引：47

作者：

Hashmi, A. Stephen K. ^{[1
]}

Kurpejovic, Elzen ^{[1
]}

Woelfle, Michael ^{[1
]}

Frey, Wolfgang ^{[1
]}

Bats, Jan W. ^{[1
]}

机构：

[1] Univ Stuttgart, Inst Organ Chem, D-70569 Stuttgart, Germany

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2007年 / 349卷 / 10期

关键词：

alkynes; furans; gold; heterocycles; homogeneous; catalysis; oxepines;

D O I：

10.1002/adsc.200600653

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A ketal group in a furyl position affords arene oxides from gamma-alkynylfurans even with the simple gold(III) chloride (AuCl3) catalyst. These can either undergo Diels-Alder reactions, isomerise to stable oxepines by an oxygen-walk reaction or by the addition of water selectively be converted to phenols which differ in the position of the hydroxy group from the normal phenols formed in the gold-catalysed phenol synthesis. With a phenyl substituent on the furan, the 2-hydroxymethylpyridinato-gold(III) complex, not the usual arene oxide but an oxepine is obtained, still the arene oxide can be trapped from the valence-tautomeric equilibrium by a Diels-Alder reaction.

引用

页码：1743 / 1750

页数：8

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