General synthesis of thiophene and selenophene-based heteroacenes

Toshihiro Okamoto; Kenichi Kudoh; Atsushi Wakamiya; Shigehiro Yamaguchi

doi:10.1021/ol0523650

General synthesis of thiophene and selenophene-based heteroacenes

Org Lett. 2005 Nov 10;7(23):5301-4. doi: 10.1021/ol0523650.

Authors

Toshihiro Okamoto¹, Kenichi Kudoh, Atsushi Wakamiya, Shigehiro Yamaguchi

Affiliation

¹ Department of Chemistry, Graduate School of Science, Nagoya University, and SORST, Japan Science and Technology Agency, Chikusa, Nagoya 464-8602, Japan.

PMID: 16268563
DOI: 10.1021/ol0523650

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.