Copper(II)‐Mediated Intramolecular Cyclization of ( Z )‐Chalcogenoenynes: Synthesis of 3‐Halochalcogenophene Derivatives | Zendy

Barancelli Daniela A. | Zendy; Schumacher Ricardo F. | Zendy; Leite Marlon R. | Zendy; Zeni Gilson | Zendy

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

Author(s) -

Barancelli Daniela A.,

Schumacher Ricardo F.,

Leite Marlon R.,

Zeni Gilson

Publication year - 2011

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.201100992

Subject(s) - chemistry , intramolecular force , yield (engineering) , palladium , copper , derivative (finance) , substrate (aquarium) , boronic acid , medicinal chemistry , suzuki reaction , coupling reaction , combinatorial chemistry , catalysis , organic chemistry , materials science , economics , financial economics , oceanography , metallurgy , geology

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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