One-Pot Synthesis Using the Supported Reagent System Na2CO3/SiO2-PPA/SiO2: Synthesis of Benzo[b]thiophenes and Naphthothiophenes

Tadashi Aoyama; Mami Orito; Toshio Takido; Mitsuo Kodomari

doi:10.1055/s-2008-1067105

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Synthesis 2008(13): 2089-2099
DOI: 10.1055/s-2008-1067105

PAPER

One-Pot Synthesis Using the Supported Reagent System Na₂CO₃/SiO₂-PPA/SiO₂: Synthesis of Benzo[b]thiophenes and Naphthothiophenes

Tadashi Aoyama*^a, Mami Orito^a, Toshio Takido^a, Mitsuo Kodomari^b
^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, Toyosu, Koto-ku, Tokyo 135-8548, Japan

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Publication History

Received 19 March 2008
Publication Date:
21 May 2008 (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 arenethiols and α-halo ketones using Na₂CO₃/SiO₂-PPA/SiO₂. Reaction of α-halo ketones with arenethiols is promoted by Na₂CO₃/SiO₂ to afford α-sulfanyl ketones, which cyclize in the presence of PPA/SiO₂ to give the corresponding thiophene-fused arenes in one-pot. The reaction using α-bromo acetals instead of α-halo ketones also gave the corresponding naphtho[2,1-b]thiophenes via a three-step reaction in one-pot.

Key words

one-pot synthesis - benzothiophenes - naphthothiophenes - supported reagents - acid-base coexistence reaction

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