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Synthesis 2008(6): 985-989  
DOI: 10.1055/s-2008-1032190
PAPER
© Georg Thieme Verlag Stuttgart · New York

A New Versatile Synthesis of 2,5-Disubstituted 3-(Methylsulfanyl)thiophenes

Claudia Fattuoni*, Michele Usai, Enzo Cadoni, M. Grazia Cabiddu, 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;
Further Information

Publication History

Received 3 December 2007
Publication Date:
28 February 2008 (online)

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Abstract

A one-pot regioselective functionalization of 3-(methylsulfanyl)thiophene with different electrophiles at the 2- and 5-positions is reported. Proper selection of the experimental conditions allows the preparation of polysubstituted products not otherwise easily available.

Key words

thiophene - regioselectivity - metalations - lithiation - carbanions­

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