Issue 6, 2018

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

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.

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

Supplementary files

Article information

Article type
Communication
Submitted
27 nov. 2017
Accepted
21 déc. 2017
First published
21 déc. 2017

Chem. Commun., 2018,54, 662-665

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 and D. W. Stephan, Chem. Commun., 2018, 54, 662 DOI: 10.1039/C7CC09128A

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