Decarbonylative Dibromination of 5-Phenylthiophene-2-carbaldehyde with Bromine

Abstract

The decarbonylative dibromination of 2-thiophenecarboxaldehyde derivatives with bromine under mild conditions is developed. The mechanism for the decarbonylation is investigated by experimental and instrumental techniques and is extended by a computational study. Alongside removal of the formyl group, this method enables functionalization of the starting compounds in a single reaction step, which can be further exploited for the synthesis of 2,5-diaryl-3-bromothiophenes and 2,3,5-triarylthiophenes.

Key words

deformylation - thiophene - reaction mechanism - Wheland intermediate - Suzuki–Miyaura reaction

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