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Synthesis 2006(22): 3855-3858  
DOI: 10.1055/s-2006-950303
PAPER
© Georg Thieme Verlag Stuttgart · New York

One-Step Polyfunctionalization of (Methylthio)thiophenes

Claudia Fattuoni*, Michele Usai, Maria G. Cabiddu, Enzo Cadoni, Stefania De Montis, Salvatore Cabiddu
Dipartimento di Scienze Chimiche, Università di Cagliari, Cittadella Universitaria di Monserrato, SS. 554, Bivio per Sestu, 09042 Monserrato (CA), Italy
Fax: +39(070)6754388; e-Mail: cfattuon@unica.it;
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Publication History

Received 6 July 2006
Publication Date:
09 October 2006 (online)

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Abstract

The one-step polyfunctionalization of 2- and 3-(methylthio)thiophenes was investigated. Direct polymetalation with superbases followed by quenching with an appropriate electrophile led to 2,αS-disubstituted derivatives starting from 2-(methyl­thio)thiophene, and 2,5,αS-trisubstituted derivatives starting from 3-(methylthio)thiophene.

Key words

heterocycles - metalation - regioselectivity - superbases - thiophenes

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