Herein we report the development of palladium-catalyzed aryl difluoromethylation via a decarbonylative cross-coupling reaction between commercially aviailable difluoroacetyl fluoride and aryl boronate esters. Stoichiometric experiments using <sup>19</sup>F NMR analysis validated the plausibility of the proposed catalytic steps and uncovered the unique decarbonylative activity of our difluoroacyl-palladium complex to compared to the related trifluoroacyl-palladium complex. A rigorous DFT study further explores the exceptional decarbonylative activity of the difluoromethyl group in our system and is in fully agreement with experimental findings. These studies provide a promising avenue for the further advancement of challenging catalytic decarbonylative fluoroalkylation protocols.

Palladium-catalyzed decarbonylative electrophilic difluoromethylation of arenes using difluoroacetyl fluoride

ACS Spring Meeting 2021

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