Palladium-Catalyzed Direct Arylation of Selenophene | Zendy

Daniel S. Rampon | Zendy; Ludger A. Wessjohann | Zendy; Paulo H. Schneider | Zendy

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Palladium-Catalyzed Direct Arylation of Selenophene

Author(s) -

Daniel S. Rampon,

Ludger A. Wessjohann,

Paulo H. Schneider

Publication year - 2014

Publication title -

the journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.2

H-Index - 228

eISSN - 1520-6904

pISSN - 0022-3263

DOI - 10.1021/jo500094t

Subject(s) - regioselectivity , palladium , metalation , aryl , chemistry , deprotonation , combinatorial chemistry , catalysis , yield (engineering) , halide , aryl halide , organic chemistry , materials science , ion , alkyl , metallurgy

An efficient and convenient method was developed for the regioselective formation of 2-aryl- or 2,5-diarylselenophenes via a palladium-catalyzed direct arylation. This protocol is suitable for a wide range of aryl halides containing different functional groups. The 2-arylated substrates can undergo an additional regioselective direct arylation event furnishing symmetrical or unsymmetrical 2,5-diaryl selenophenes in good yield. Competition experiments and the role of the acid additive are in agreement with a concerted metalation deprotonation (CMD) pathway.

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