Difluoromethane as a precursor to difluoromethyl borates. Issue 35 (10th April 2019)

• Record Type: Journal Article
• Authors: Geri, Jacob B.; Aguilera, Ellen Y.; Szymczak, Nathaniel K.
• Is Part Of: Chemical communications. Volume 55:Issue 35(2019)
• Page Start: 5119
• Page End: 5122
• Publication Date: 2019-04-10
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1039/c9cc01565e
• Languages: English
• ISSNs: 1359-7345

Abstract

Abstract : Difluoromethane (CF2 H2 ) is an ecologically-friendly refrigerant which holds promise as a source of CF2 H − . This manuscript demonstrates a Lewis acid/base pair approach to deprotonate CF2 H2 and capture CF2 H − as a strategy to enable subsequent difluoromethylation. Abstract : Difluoromethane (CF2 H2 ) is an ecologically-friendly refrigerant which holds promise as a source of CF2 H − . However, the weak acidity (p K a = 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 CF2 H2 and capture CF2 H − as R3 B–CF2 H − adducts. One reagent can be used as a base-free Suzuki reagent in palladium-mediated difluoromethylation, where CF2 H − transfer is templated by precoordination to an azaborine derived R3 B–CF2 H − reagent.