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Highly Site-Selective Direct C–H Bond Functionalization of Phenols with α-Aryl-α-diazoacetates and Diazooxindoles via Gold Catalysis
Zhunzhun Yu , Ben Ma , Mingjin Chen , Hai-Hong Wu , Lu Liu *, and Junliang Zhang *
Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, East China Normal University, 3663 North Zhongshan Road, Shanghai 200062, China

J. Am. Chem. Soc., 2014, 136 (19), pp 6904–6907
DOI: 10.1021/ja503163k
Publication Date (Web): April 29, 2014
Copyright © 2014 American Chemical Society
*E-mail: lliu@chem.ecnu.edu.cn., *E-mail: jlzhang@chem.ecnu.edu.cn.
Section:
General Organic Chemistry

Abstract

An unprecedented direct C–H bond functionalization of unprotected phenols with α-aryl α-diazoacetates and diazooxindoles was developed. A tris(2,4-di-tert-butylphenyl) phosphite derived gold complex promoted the highly chemoselective and site-selective C–H bond functionalization of phenols and N-acylanilines with gold-carbene generated from the decomposition of diazo compounds, furnishing the corresponding products in moderate to excellent yields at rt. The salient features of this reaction include readily available starting materials, unprecedented C–H functionalization rather than X–H insertion, good substrate scope, mild conditions, high efficiency, and ease in further transformation. To the best of our knowledge, this is the first example of C–H functionalization of unprotected phenols with diazo compounds.

http://pubs.acs.org/doi/abs/10.1021/ja503163k

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