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Synlett 2005(7): 1137-1141  
DOI: 10.1055/s-2005-865211
LETTER
© Georg Thieme Verlag Stuttgart · New York

A Novel and Efficient Approach to (Z)-1,2-Bis(benzodithienyl)ethene ­Precursors of Tetrathia[7]helicenes

Clara Baldolia, Alberto Bossib, Clelia Gianninib, Emanuela Licandro*b, Stefano Maioranab, Dario Perdicchiab, Michele Schiavob
a C.N.R., Istituto di Scienze e Tecnologie Molecolari, Via C. Golgi, 19, 20133 Milan, Italy
b Dipartimento di Chimica Organica e Industriale e Centro Interdisciplinare Materiali e Interfacce Nanostrutturati (C.I.M.A.I.N.A.), Univesità degli Studi di Milano, Via C. Golgi, 19, 20133 Milan, Italy
Fax: +39(02)50314139; e-Mail: emanuela.licandro@unimi.it;
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Publication History

Received 20 December 2004
Publication Date:
14 April 2005 (online)

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Abstract

A new and efficient method for the ‘one-step’ synthesis of (Z)-1,2-bis(benzodithienyl)ethenes has been set up using double Suzuki coupling between stereochemically defined diboronic acid esters and 2-iodo-benzodithiophene. The new Z-alkenes thus obtained can be easily and efficiently photochemically cyclised to the newly substituted tetrathia[7]helicenes.

Key words

coupling - helical structures - fused ring systems - (Z)-1,2-bis(benzodithiophenyl)ethenes - thiahelicenes

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9

Sigma-Aldrich company sells several (Z)-diboronic acid esters.