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Palladium-Catalyzed Direct Arylation of Selenophene
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