Issue 24, 2013
From the journal:

Organic & Biomolecular Chemistry

Trace amount Cu (ppm)-catalyzed intramolecular cyclization of 2-(gem-dibromovinyl)phenols(thiophenols) to 2-bromobenzofurans(thiophenes)†

Yong Ji,a   Pinhua Li,b   Xiuli Zhang*ac  and  Lei Wang*bc  

* Corresponding authors

a Department of Chemistry, Anhui Agricultural University, Hefei, Anhui 230036, P. R. China
E-mail: zhxiuli@163.com

b Department of Chemistry, Huaibei Normal University, Huaibei, Anhui 235000, P. R. China
E-mail: leiwang@chnu.edu.cn
Fax: +86-561-309-0518
Tel: +86-561-380-2069

c State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, P. R. China

Abstract

An intramolecular cyclization of 2-(gem-dibromovinyl)phenols(thiophenols) to give 2-bromobenzofurans(thiophenes) in the presence of a trace amount of Cu (0.0064 mol%, 25 ppm) has been developed. The reaction provides the desired products in excellent yields under fluoride-free and mild reaction conditions and with a TON (turnover number) of up to 1.5 × 104.

Graphical abstract: Trace amount Cu (ppm)-catalyzed intramolecular cyclization of 2-(gem-dibromovinyl)phenols(thiophenols) to 2-bromobenzofurans(thiophenes)

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Article information

DOI
https://doi.org/10.1039/C3OB40531A
Article type
Paper
Submitted
16 Mar 2013
Accepted
12 Apr 2013
First published
16 Apr 2013

Org. Biomol. Chem., 2013,11, 4095-4101

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Trace amount Cu (ppm)-catalyzed intramolecular cyclization of 2-(gem-dibromovinyl)phenols(thiophenols) to 2-bromobenzofurans(thiophenes)

Y. Ji, P. Li, X. Zhang and L. Wang, Org. Biomol. Chem., 2013, 11, 4095 DOI: 10.1039/C3OB40531A

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