Cost-Efficient, Multigram Scalable Synthesis of Shelf-Stable Electrophilic (Phenylsulfonyl)difluoromethylating Reagents
Résumé
An easy-to-handle protocol for the synthesis of an efficient electrophilic (phenylsulfonyl)difluoromethylating reagent, namely, the S-([phenylsulfonyl]difluoromethyl)-dibenzothiophenium salt I, is depicted. The latter was synthesized on approximately 40 g scale in a three-step/one-purification sequence from commercially available or easy-to-synthesize starting materials with an estimated global prize of about 10.6 €/g. The bench-stable reagent I was found to be air- and moisture-tolerant. By changing the counter anion, a small library of electrophilic sources (reagents I–III) is now available for the (phenylsulfonyl)difluoromethylation reaction. Differential scanning calorimetry (DSC) measurements have been also carried out on the different salts (I–III) along with a key intermediate to ensure a safe process.
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