A non-photochemical route to synthesize simple benzo[1,2-b:4,3-b′]dithiophenes: FeCl3-mediated cyclization of dithienyl ethenes

Silvia Cauteruccio; Davide Dova; Claudia Graiff; Claudio Carrara; Julien Doulcet; G. Richard Stephenson; Emanuela Licandro

doi:10.1039/C3NJ01567J

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A non-photochemical route to synthesize simple benzo[1,2-b:4,3-b′]dithiophenes: FeCl₃-mediated cyclization of dithienyl ethenes†

Silvia Cauteruccio,^a Davide Dova,^a Claudia Graiff,^b Claudio Carrara,^a Julien Doulcet,^c G. Richard Stephenson^c and Emanuela Licandro*^a

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* Corresponding authors

^a Dipartimento di Chimica, Università degli Studi di Milano, via Golgi 19, I-20133 Milano, Italy
E-mail: emanuela.licandro@unimi.it
Tel: +39 0250314143

^b Dipartimento di Chimica, Università degli Studi di Parma, Viale delle Scienze 17/A, Parma, Italy

^c School of Chemistry, University of East Anglia, Norwich Research Park, Norwich, UK

Abstract

The FeCl₃-mediated cyclization of α,α′-disubstituted Z-alkenes 1 is reported as a general and non-photochemical route to synthesize benzo[1,2-b:4,3-b′]dithiophene (BDT) derivatives 2, achievable in good yields starting from cheap and easily available materials. The influence of the temperature and the nature of the substituents on the scope and limitations of this methodology is also reported.

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Article information

DOI: https://doi.org/10.1039/C3NJ01567J
Article type: Letter
Submitted: 12 Dec 2013
Accepted: 21 Feb 2014
First published: 21 Feb 2014

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New J. Chem., 2014,38, 2241-2244

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A non-photochemical route to synthesize simple benzo[1,2-b:4,3-b′]dithiophenes: FeCl₃-mediated cyclization of dithienyl ethenes

S. Cauteruccio, D. Dova, C. Graiff, C. Carrara, J. Doulcet, G. R. Stephenson and E. Licandro, New J. Chem., 2014, 38, 2241 DOI: 10.1039/C3NJ01567J

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