First synthesis of (difluoroiodomethyl)thiophenes through double iodation of 2-(difluoromethylene)but-3-yn-1-yl benzyl sulfides.

Org Biomol Chem

Department of Chemistry and Applied Chemistry, Saga University, Honjyo-machi 1, Saga 840-8502, Japan.

Published: March 2025


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Article Abstract

The Sonogashira cross-coupling of 2-bromo-3,3-difluoroallyl benzyl sulfide with various terminal acetylenes afforded the corresponding 2-(difluoromethylene)but-3-yn-1-yl benzyl sulfides in acceptable to good yields. Subsequent double iodation of the enyne sulfides in a mixed solvent (CHCl/EtOH = 50/1) provided promising 4-(difluoroiodomethyl)-3-iodo-2-substituted thiophenes in good to excellent yields.

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http://dx.doi.org/10.1039/d5ob00152hDOI Listing

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