铑催化的卤代炔烃分子内[4 + 2]环加成反应。

Rhodium-catalyzed intramolecular [4 + 2] cycloadditions of alkynyl halides.

作者信息

Yoo Woo-Jin, Allen Anna, Villeneuve Karine, Tam William

机构信息

Guelph-Waterloo Centre for Graduate Work in Chemistry and Biochemistry, Department of Chemistry, University of Guelph, Guelph, Ontario, Canada N1G 2W1.

出版信息

Org Lett. 2005 Dec 22;7(26):5853-6. doi: 10.1021/ol052412o.

DOI:10.1021/ol052412o

PMID:16354083

Abstract

[reaction: see text] Cationic rhodium(I)-catalyzed intramolecular [4 + 2] cycloadditions of diene-tethered alkynyl halides were found to occur in good yields (70-87%). The halide moiety is compatible with the cycloaddition reactions, and no oxidative insertion to the alkynyl halide was observed. The halogen-containing cycloadducts could be transformed into a variety of products that are difficult or impossible to obtain via direct cycloaddition.

摘要

[反应：见正文] 发现阳离子铑（I）催化的二烯连接的卤代炔烃的分子内[4 + 2]环加成反应能以良好的产率（70 - 87%）发生。卤化物部分与环加成反应兼容，且未观察到对卤代炔烃的氧化插入反应。含卤素的环加成产物可转化为多种通过直接环加成难以或无法获得的产物。