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Synlett 2011(7): 923-926  
DOI: 10.1055/s-0030-1259726
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

meta-Selective Substitution of Phenols with Indoles via One-Pot Oxidative Dearomatization-Michael Addition-Aromatization

Yang Yea, Hua Wanga, Renhua Fan*a,b
a Department of Chemistry, Fudan University, 220 Handan Road, Shanghai 200433, P. R. of China
Fax: +86(21)65642019; e-Mail: rhfan@fudan.edu.cn;
b Shanghai Key Laboratory of Molecular Catalysts and Innovative Materials, Department of Chemistry, Fudan University, 220 Handan Road, Shanghai 200433, P. R. of China
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Publication History

Received 3 December 2010
Publication Date:
10 March 2011 (online)

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Abstract

An oxidative coupling strategy involving hypervalent organoiodine-induced oxidative dearomatization of 4-substituted phenols, Brønsted acid catalyzed Michael addition with indoles, and aromatization has been developed. The one-pot reaction provides an efficient access to the meta-indole-substituted phenol derivatives.

Key words

aromatic substitution - biaryls - cross-coupling reaction - oxidation - regioselectivity

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