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A General and Mild Catalytic α‐Alkylation of Unactivated Esters Using Alcohols
Author(s) -
Guo Le,
Ma Xiaochen,
Fang Huaquan,
Jia Xiangqing,
Huang Zheng
Publication year - 2015
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201410293
Subject(s) - alkylation , chemistry , catalysis , primary (astronomy) , alkyl , organic chemistry , halide , pincer movement , carboxylic acid , combinatorial chemistry , physics , astronomy
Catalytic α‐alkylation of esters with primary alcohols is a desirable process because it uses low‐toxicity agents and generates water as the by‐product. Reported herein is a NCP pincer/Ir catalyst which is highly efficient for α‐alkylation of a broad scope of unactivated esters under mild reaction conditions. For the first time, alcohols alkylate unactivated α‐substituted acyclic esters, lactones, and even methyl and ethyl acetates. This method can be applied to the synthesis of carboxylic acid derivatives with diverse structures and functional groups, some of which would be impossible to access by conventional enolate alkylations with alkyl halides.