Synthesis of difluoromethyl and deuterium-labeled difluoromethyl thioethers from aliphatic electrophiles?

Chemical Communications Pub Date: 2020-03-04 DOI: 10.1039/C9CC09709K

Abstract

A one-pot difluoromethylthiolation of alkyl electrophiles with thiourea and diethyl bromodifluoromethylphosphonate is described. The transition-metal-free approach, readily available reagents, and mild conditions provide a practical way for the synthesis of difluoromethyl thioethers. By changing the “H” source to the most commonly used “D” sources CD3OD and D2O, this strategy enables efficient synthesis of SCF2D-substituted molecules in good yields with high levels of D incorporation.

Graphical abstract: Synthesis of difluoromethyl and deuterium-labeled difluoromethyl thioethers from aliphatic electrophiles
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