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Recyclable nickel-catalyzed C–H/O–H dual functionalization of phenols with mandelic acids for the synthesis of 3-aryl benzofuran-2(3H)-ones under solvent-free conditions

Authors :
Shuang-Feng Yin
Zhi Tang
Renhua Qiu
Xu Zhihui
Tong Zhou
Chak-Tong Au
Source :
Green Chemistry. 21:2015-2022
Publication Year :
2019
Publisher :
Royal Society of Chemistry (RSC), 2019.

Abstract

Herein, we developed a protocol for the efficient synthesis of 3-aryl benzofuran-2(3H)-ones under solvent-free conditions from phenols and mandelic acids using Ni(OTf)2 as a catalyst. A diverse range of mandelic acids and phenols undergo C–H/O–H bond dual functionalization to generate products in moderate to good or excellent yields. The nickel catalyst can be easily recycled in a test of three runs at the scale of 10 mmol without significant decline in the product yield. It was demonstrated that the yield of the desired product could be increased, for example, in the synthesis of the antioxidant Irganox HP-136 to a scale of 166 g.

Details

ISSN :
14639270 and 14639262
Volume :
21
Database :
OpenAIRE
Journal :
Green Chemistry
Accession number :
edsair.doi...........b18c2081396c1bcf1bb0120638d5089a
Full Text :
https://doi.org/10.1039/c9gc00305c