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. 2018 Jan 16;54(6):662-665.
doi: 10.1039/c7cc09128a.

Air- and water-stable Lewis acids: synthesis and reactivity of P-trifluoromethyl electrophilic phosphonium cations

V Fasano  1 , J H W LaFortune, J M Bayne, M J Ingleson, D W Stephan
Affiliations

Air- and water-stable Lewis acids: synthesis and reactivity of P-trifluoromethyl electrophilic phosphonium cations

V Fasano et al. Chem Commun (Camb). .

Abstract

A new class of electrophilic phosphonium cations (EPCs) containing a -CF3 group attached to the phosphorus(v) center is readily accessible in high yields, via a scalable process. These species are stable to air, water, alcohol and strong Brønsted acid, even at raised temperatures. Thus, P-CF3 EPCs are more robust than previously reported EPCs containing P-X moieties (X = F, Cl, OR), and despite their reduced Lewis acidity they function as Lewis acid catalysts without requiring anhydrous reaction conditions.

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