Organic Letters 2005-11-10

General synthesis of thiophene and selenophene-based heteroacenes.

Toshihiro Okamoto, Kenichi Kudoh, Atsushi Wakamiya, Shigehiro Yamaguchi

Index: Org. Lett. 7(23) , 5301-4, (2005)

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Abstract

[reaction: see text] A new intramolecular triple cyclization of bis(o-haloaryl)diacetylenes, via dilithiation followed by reaction with chalcogen elements, produces pi-conjugated compounds containing heterole-1,2-dichalcogenin-heterole fused tricyclic skeletons. The subsequent dechalcogenation with copper metal affords a series of thiophene- and selenophene-based heteroacenes.