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Difluoromethane as a precursor to difluoromethyl borates
- GeriCurrent address: Merck Center for Catalysis at Princeton University, Washington Road, Princeton, NJ 08544, USA., Jacob B., Aguilera, Ellen Y., Szymczak, Nathaniel K.
- Chemical communications 2019 v.55 no.35 pp. 5119-5122
- acidity, borates, chemical reactions, feedstocks
- Difluoromethane (CF₂H₂) is an ecologically-friendly refrigerant which holds promise as a source of CF₂H⁻. However, the weak acidity (pKₐ = 35–41) and low stability of the conjugate base have prevented its utilization as a chemical feedstock. In this manuscript, we use a Lewis pair approach to deprotonate CF₂H₂ and capture CF₂H⁻ as R₃B–CF₂H⁻ adducts. One reagent can be used as a base-free Suzuki reagent in palladium-mediated difluoromethylation, where CF₂H⁻ transfer is templated by precoordination to an azaborine derived R₃B–CF₂H⁻ reagent.