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.
Air- and water-stable Lewis acids: Synthesis and reactivity of P-trifluoromethyl electrophilic phosphonium cations / V. Fasano, J.H.W. Lafortune, J.M. Bayne, M.J. Ingleson, D.W. Stephan. - In: CHEMICAL COMMUNICATIONS. - ISSN 1359-7345. - 54:6(2018 Jan 18), pp. 662-665. [10.1039/c7cc09128a]
Air- and water-stable Lewis acids: Synthesis and reactivity of P-trifluoromethyl electrophilic phosphonium cations
V. FasanoPrimo
;
2018
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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