Synthesis of Phenyl-2,2′-bichalcophenes and Their Aza-Analogues by Catalytic Oxidative Deacetylation

^† These authors contributed equally to this work.

Abstract

Efficient synthetic method for medicinally and opto-electronically important bichalcophenes is reported, which highlights Mn(OAc)₃/CoCl₂-catalyzed oxidative deacetylation of 1,5-dicarbonyl compounds that were easily prepared by conjugate addition of ethyl acetoacetate to α,β-unsaturated carbonyl compounds containing a chalcophene unit. Paal–Knorr reaction of the resulting 1,4-dicarbonyl compounds produced 4-phenyl-2,2′-bichalcophenes and their aza-analogues.

Key words

bichalcophene - catalytic oxidation - deacetylation - 1,4-dicarbonyl compound - Paal–Knorr reaction

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