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Pd-Catalyzed Difluoromethylations of Aryl Boronic Acids, Halides, and Pseudohalides with ICF2H Generated ex Situ

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An expedient ex-situ generation of difluoroiodomethane (DFIM) and its immediate use in a Pd-catalyzed difluoromethylation of aryl boronic acids and ester derivatives in a two-chamber reactor is reported. Heating a solution of bromodifluoroacetic acid with sodium iodide in sulfolane proved to be effective for the generation of near stoichiometric amounts of DFIM for the ensuing catalytic coupling step. A two-step difluoromethylation of aryl (pseudo)halides with tetrahydroxydiboron as a low-cost reducing agent, both promoted by Pd catalysis, proved effective to install this fluorine-containing C1 group onto several pharmaceutically relevant molecules. Finally, the method proved adaptable to deuterium incorporation by simply adding D2O to the DFIM-generating chamber.
OriginalsprogEngelsk
Artikelnummere202200997
TidsskriftChemistry - A European Journal
Vol/bind28
Nummer34
Antal sider6
ISSN0947-6539
DOI
StatusUdgivet - jun. 2022

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© 2022 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH.

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