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Issue 3, 2016
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A diversity-oriented synthesis of bioactive benzanilides via a regioselective C(sp2)–H hydroxylation strategy

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Abstract

A diversity-oriented synthesis of bioactive benzanilides via C(sp2)–H hydroxylation has been studied. Different regioselectivity was observed with Ru(II) and Pd(II) catalysts. The reaction demonstrates excellent regioselectivity, good tolerance of functional groups, and high yields. A wide range of ortho-hydroxylated-benzanilides can be readily synthesized with excellent regioselectivity via this new synthetic strategy. Computational investigations revealed that the regioselectivity was controlled mainly by both steric and electronic factors. Steric effects determine the regioselective outcomes in the Ru-catalyzed reaction, while electronic effects are dominant in the Pd-catalyzed reaction.

Graphical abstract: A diversity-oriented synthesis of bioactive benzanilides via a regioselective C(sp2)–H hydroxylation strategy

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Supplementary files

Article information


Submitted
15 Oct 2015
Accepted
03 Dec 2015
First published
03 Dec 2015

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2016,7, 2229-2238
Article type
Edge Article

A diversity-oriented synthesis of bioactive benzanilides via a regioselective C(sp2)–H hydroxylation strategy

Y. Sun, T. Sun, Y. Wu, X. Zhang and Y. Rao, Chem. Sci., 2016, 7, 2229
DOI: 10.1039/C5SC03905C

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