Journal
JOURNAL OF FLUORINE CHEMISTRY
Volume 208, Issue -, Pages 10-14Publisher
ELSEVIER SCIENCE SA
DOI: 10.1016/j.jfluchem.2018.01.009
Keywords
Difluoromethylation; Aromatic aldehydes; TMSCF3; Lithium iodide; Ruppert-Prakash reagent; Lithium tetrafluoroborate
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Funding
- Loker Hydrocarbon Research Institute
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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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