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C-H Electrophilic (phenylsulfonyl)difluoromethylation of (hetero)arenes with a newly designed reagent.

ABSTRACT: The synthesis of an original electrophilic difluoromethylating reagent was successfully achieved upon a straightforward protocol (3 steps). Like a Swiss army knife, this bench-stable reagent allowed the functionalization of various classes of compounds under mild and transition metal-free conditions. Hence, an efficient and operationally simple tool for the construction of C(sp²)-, C(sp³)- and S-CF₂SO₂Ph bonds was provided, expanding the chemical space of PhSO₂CF₂-containing molecules. Late-stage functionalization of bioactive molecules and the synthesis of PhSO₂CF₂- and HCF₂-analogs of Lidocaine were also successfully achieved.

SUBMITTER: Nobile E

PROVIDER: S-EPMC8603193 | biostudies-literature | 2021 Nov

REPOSITORIES: biostudies-literature

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C-H Electrophilic (phenylsulfonyl)difluoromethylation of (hetero)arenes with a newly designed reagent.

Nobile Enzo E Castanheiro Thomas T Besset Tatiana T

Chemical communications (Cambridge, England) 20211119 92

The synthesis of an original electrophilic difluoromethylating reagent was successfully achieved upon a straightforward protocol (3 steps). Like a Swiss army knife, this bench-stable reagent allowed the functionalization of various classes of compounds under mild and transition metal-free conditions. Hence, an efficient and operationally simple tool for the construction of C(sp2)-, C(sp3)- and S-CF2SO2Ph bonds was provided, expanding the chemica ...[more]

PMID: 34747423

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