Gold(I)-Catalyzed Rearrangement of Propargyl Benzyl Ethers: A Practical Method for the Generation and in Situ Transformation of Substituted Allenes

被引：115

作者：

Bolte, Benoit ^{[1
]}

Odabachian, Yann ^{[1
]}

Gagosz, Fabien ^{[1
]}

机构：

[1] Ecole Polytech, CNRS, Dept Chim, UMR 7652, F-91128 Palaiseau, France

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2010年 / 132卷 / 21期

关键词：

H BOND FUNCTIONALIZATION; ORGANIC-SYNTHESIS; ALKYNYL ETHERS; GOLD; CATALYSIS; CYCLOISOMERIZATION; HYDROALKYLATION; CYCLIZATION; PLATINUM; ENYNES;

D O I：

10.1021/ja1020469

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A series of benzyl propargyl ethers react with a gold(I) catalyst to furnish variously substituted allenes via a 1,5-hydride shift/fragmentation sequence. This transformation is rapid and practical. It can be performed under very mild conditions (room temperature or 60 C) using terminal as well as substituted alkyne substrates bearing a primary, secondary, or tertiary benzyl ether group. The allenes thus formed can be reacted in situ with an internal or external nucleophile, corresponding to an overall reductive substitution process, to produce more functionalized compounds.

引用

页码：7294 / +

页数：4

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