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Bu 4 NI‐Catalyzed and t BuOOH‐Oxidized Esterification of Aldehydes with Alkyl Halides in Water
Author(s) -
Wang QianQian,
Wang ZhangXin,
Xu YuanShuang,
Zhang XinYing,
Fan XueSen
Publication year - 2016
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201600342
Subject(s) - chemistry , alkyl , halide , catalysis , organic chemistry , intramolecular force , substrate (aquarium) , solvent , inert gas , inert , combinatorial chemistry , geology , oceanography
The importance of esters has stimulated significant efforts to develop efficient methods for their synthesis. In this study, an oxidative esterification of aldehydes with alkyl halides by using tert ‐butyl hydroperoxide as an oxidant, Bu 4 NI as catalyst, and water as solvent is presented. Notably, this novel esterification protocol is suitable for both aromatic and aliphatic aldehydes, primary and secondary alkyl halides to give ester products with broad structural diversity. Through an intramolecular version of this novel esterification process, an alternative synthetic approach toward the biologically interesting isobenzofuran‐1(3 H )‐one was also realized. Compared with literature procedures, the synthetic strategies developed herein showed advantages such as direct use of commercially available and economical starting materials, wide substrate scope, good tolerance of functional groups, sustainable oxidant, and no need of an inert atmosphere or dry solvents.