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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.
Original languageEnglish
Article numbere202200997
JournalChemistry - A European Journal
Number of pages6
Publication statusPublished - Jun 2022

Bibliographical note

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

    Research areas

  • aryl boronic acids, deuterium labeling, difluoroiodomethane, difluoromethylation, palladium catalysis

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