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Copper(II)-Mediated Intramolecular Cyclization of (Z)-Chalcogenoenynes: Synthesis of 3-Halochalcogenophene Derivatives

✍ Scribed by Daniela A. Barancelli; Ricardo F. Schumacher; Marlon R. Leite; Gilson Zeni

Publisher
John Wiley and Sons
Year
2011
Tongue
English
Weight
446 KB
Volume
2011
Category
Article
ISSN
1434-193X

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✦ Synopsis

Abstract

We present our results on the cyclization of (Z)‐chalcogenoenynes mediated by copper(II) salts to afford 3‐halochalcogenophenes in satisfactory yields through an intramolecular 5‐endo‐dig cyclization. The methodology was carried out using CuCl~2~ at 50 °C or CuBr~2~ at room temperature under an ambient atmosphere. The reaction took place under very mild reaction conditions and tolerated considerable functionality. One 3‐bromo‐selenophene derivative was applied as a substrate in the palladium‐catalyzed cross‐coupling reaction with a boronic acid to give the Suzuki type product in good yield.

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