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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http://dx.doi.org/10.1021/ol9010745 | DOI Listing |
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