Synlett 2005(18): 2739-2742  
DOI: 10.1055/s-2005-918928
LETTER
© Georg Thieme Verlag Stuttgart · New York

One-Pot Synthesis of Benzo[b]thiophenes and Naphtho[2,1-b]thiophenes in the Presence of Acidic and Basic Supported Reagents

Tadashi Aoyama*a, Toshio Takidoa, Mitsuo Kodomarib
a Department of Materials and Applied Chemistry, College of Science and Technology, Nihon University, Kanda Surugadai, Chiyoda-ku, Tokyo 101-8308, Japan
Fax: +81(3)32590818; e-Mail: aoyama@chem.cst.nihon-u.ac.jp;
b Department of Applied Chemistry, Shibaura Institute of Technology, Shibaura, Minato-ku, Tokyo 108-8548, Japan
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Publication History

Received 28 July 2005
Publication Date:
10 October 2005 (online)

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Abstract

A simple and efficient method has been developed for the synthesis of benzo[b]thiophenes and naphtho[2,1-b]thiophenes from aryl thiols and α-halo ketones by using an acid- and a base-supported reagent system, Na2CO3/SiO2-PPA/SiO2. Reaction of α-halo ketones with aryl thiols is promoted by Na2CO3/SiO2 to afford α-phenylthio ketones, which cyclizes in the presence of PPA/SiO2 to give the corresponding arylthiophenes in one-pot.