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Synthesis 2011(20): 3364-3370  
DOI: 10.1055/s-0030-1260202
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Regioselective Carbon-Carbon Bond Formation in the Reaction of 2-Hydroxy-2-(trifluoromethyl)-2H-chromenes with Indoles Promoted by Lewis Acid

Wan Panga,b, Jian Wei Hanb, Jing Wei Zhaob, Shi Zheng Zhu*b
a School of Chemical and Environmental Engineering, Shanghai Institute of Technology, 120 Caobao Lu, Shanghai 200235, P. R. of China
b Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, P. R. of China
Fax: +86(21)64166128; e-Mail: zhusz@mail.sioc.ac.cn;
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Publication History

Received 7 June 2011
Publication Date:
05 September 2011 (online)

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Abstract

A simple and efficient Lewis acid mediated C-C coupling reaction between readily available 2-hydroxy-2-(trifluoro­methyl)-2H-chromenes and various indoles via regioselective nucleophilic substitution has been developed. On the basis of this methodology, a series of bio- and pharmacologically important 2- and 4-functionalized 2-(trifluoromethyl)-2H-chromenes were prepared in high yields.

Key words

regioselective - C-C bond formation - 2H-chromenes - indoles - Lewis acid