Cost-Efficient, Multigram Scalable Synthesis of Shelf-Stable Electrophilic (Phenylsulfonyl)difluoromethylating Reagents - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Organic Process Research and Development Année : 2022

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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hal-03744654 , version 1 (16-11-2022)

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Enzo Nobile, Jean-Pierre Hébert, Thomas Castanheiro, Alain Ledoux, Tatiana Besset. Cost-Efficient, Multigram Scalable Synthesis of Shelf-Stable Electrophilic (Phenylsulfonyl)difluoromethylating Reagents. Organic Process Research and Development, 2022, 26 (8), pp.2415-2422. ⟨10.1021/acs.oprd.2c00099⟩. ⟨hal-03744654⟩
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