铟-铜和铟-银介导的醛与未活化卤代烃在水中的巴比耶-格氏型烷基化反应。

Indium-copper and indium-silver mediated barbier-grignard-type alkylation reaction of aldehydes using unactivated alkyl halides in water.

作者信息

Shen Zhi-Liang, Yeo Yan-Lin, Loh Teck-Peng

机构信息

Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore.

出版信息

J Org Chem. 2008 May 16;73(10):3922-4. doi: 10.1021/jo8000589. Epub 2008 Apr 9.

DOI:10.1021/jo8000589

PMID:18396908

Abstract

An efficient method has been developed for the Barbier-Grignard-type alkylation reaction of aldehydes (including aliphatic version) using unactivated alkyl halides in water in the presence of an In/CuI/I(2) or In/AgI/I(2) system. The reactions proceeded more efficiently in water than in organic solvent. In, CuI or AgI, and I(2) were all essential for the efficient progress of the reactions. A radical-type reaction mechanism was studied and proposed by using 4-pentenal as substrate.

摘要

已开发出一种高效方法，用于醛（包括脂肪族醛）的巴比耶 - 格氏型烷基化反应，该反应在水相中，在In/CuI/I₂或In/AgI/I₂体系存在下，使用未活化的卤代烃进行。该反应在水中比在有机溶剂中进行得更高效。In、CuI或AgI以及I₂对于反应的高效进行都是必不可少的。以4-戊烯醛为底物研究并提出了一种自由基型反应机理。