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Synthesis 2016; 48(24): 4423-4430
DOI: 10.1055/s-0035-1562615
DOI: 10.1055/s-0035-1562615
paper
Decarbonylative Dibromination of 5-Phenylthiophene-2-carbaldehyde with Bromine
Further Information
Publication History
Received: 03 June 2016
Accepted after revision: 14 July 2016
Publication Date:
24 August 2016 (online)
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 reactionSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1562615.
- Supporting Information
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