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N‐Heterocyclic Carbene‐Catalyzed Oxidative Esterification Reaction of Aldehydes with Alkyl Halides under Aerobic Conditions
Author(s) -
Xin YangChun,
Shi ShiHui,
Xie DongDong,
Hui XinPing,
Xu PengFei
Publication year - 2011
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201100937
Subject(s) - chemistry , alkyl , halide , carbene , electrophile , catalysis , organic chemistry , medicinal chemistry , beta hydride elimination
An efficient N‐heterocyclic carbene‐catalyzed oxidative esterification reaction of aldehydes with alkyl halides or alkyl 4‐methylbenzenesulfonate is reported. It was worth noting that (1) the configuration of alkyl halides or alkyl 4‐methylbenzenesulfonates was inverted completely, and (2) the presence of oxygen was crucial for this transformation. The reaction proceeded smoothly under mild conditions and various esters were afforded in moderate to good yields. In addition, we have developed an efficient tandem oxidation/esterification reaction of alcohols. This methodology provides a rare example of a reaction of the Breslow intermediate to sp 3 ‐carbon centered electrophiles.