Nucleophilic difluoromethylation of aromatic aldehydes using trimethyl(trifluoromethyl)silane (TMSCF3)

Add time:07/28/2019    Source:sciencedirect.com

Reaction of the Ruppert–Prakash reagent (Me3SiCF3) with aromatic aldehydes in the presence of triphenylphosphine, lithium iodide and lithium tetrafluoroborate selectively furnishes gem-difluorinated phosphonium salts. Simple alkaline hydrolysis of these salts results in difluoromethylated products. Thus, one-pot nucleophilic difluoromethylation of aromatic aldehydes using Me3SiCF3 has been accomplished. The protocol tolerates electron withdrawing as well as electron donating substituents.

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