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Metal-Free Coupling of 2-Vinylphenols and Carboxylic Acids: An Access to 3-Acyloxy-2,3-dihydrobenzofurans

Authors :
Ying Shao
Hao Zheng
Xiaobing Wan
Jiang Cheng
Jijun Chen
Source :
The Journal of Organic Chemistry. 80:10734-10741
Publication Year :
2015
Publisher :
American Chemical Society (ACS), 2015.

Abstract

A new coupling reaction between 2-vinylphenols and carboxylic acids was developed to synthesize 3-acyloxy-2,3-dihydrobenzofurans using Bu4NI as a catalyst and t-BuOOH as an oxidant. This simple and practical methodology is notable due to the ability to complete it under metal-free conditions, with easily available precursors, resulting in a product with high atom economy and high functional group tolerance. Upon the basis of experimental observations and literature, a plausible mechanism is proposed.

Details

ISSN :
15206904 and 00223263
Volume :
80
Database :
OpenAIRE
Journal :
The Journal of Organic Chemistry
Accession number :
edsair.doi.dedup.....ea3a23ca30a983f939ea4603cea338bc
Full Text :
https://doi.org/10.1021/acs.joc.5b01941