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Synthesis of Fused 4-Iodoselenophene[2,3-b]thiophenes by Electrophilic Cyclization of 3-Alkynylthiophenes

✍ Scribed by André L. Stein; Juliana da Rocha; Paulo Henrique Menezes; Gilson Zeni

Publisher
John Wiley and Sons
Year
2010
Tongue
English
Weight
494 KB
Volume
2010
Category
Article
ISSN
1434-193X

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✦ Synopsis

Abstract

We present here our results on the electrophilic cyclization reaction of 3‐alkynylthiophenes with different electrophiles such as I~2~, ICl, and PhSeBr. The cyclization reaction proceeded cleanly under mild reaction conditions, giving fused 4‐iodoselenophene[2,3‐b]thiophenes in excellent yields. In addition, the obtained chalcogenophenes were readily transformed into more complex products through palladium‐ or copper‐catalyzed cross‐coupling reactions with thiols, boronic acids, and organozinc reagents.

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