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Facile and scalable synthesis of the fused-ring heterocycles thieno[3,2-b]thiophene and thieno[3,2-b]furan

Facile and scalable synthesis of the fused-ring heterocycles thieno[3,2-b]thiophene and thieno[3,2-b]furan

Organic Letters 11(14): 3144-3147

An optimized synthetic methodology which allows for efficient and scalable access to the important fused-ring heterocycle thieno[3,2-b]thiophene and the first reported isolation of thieno[3,2-b]furan is presented. The properties of thieno[3,2-b]furan were assessed through a detailed analysis of the NMR data and an investigation of the chemical reactivity. Thieno[3,2-b]furan is chemically robust and offers good selectivity toward functionalization at the 2-position via bromination and the 5-position via deprotonation.

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Accession: 053186261

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PMID: 19548691

DOI: 10.1021/ol9010745

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