Difluoromethane as a precursor to difluoromethyl borates.

Difluoromethane as a precursor to difluoromethyl borates.

Geri, Jacob B;Aguilera, Ellen Y;Szymczak, Nathaniel K;
Chemical communications (Cambridge, England) 2019 Vol. 55 pp. 5119-5122
183
geri2019difluoromethanechemical

Abstract

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.

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49044
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