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Issue 6, 2018
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Air- and water-stable Lewis acids: synthesis and reactivity of P-trifluoromethyl electrophilic phosphonium cations

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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

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Publication details

The article was received on 27 Nov 2017, accepted on 21 Dec 2017 and first published on 21 Dec 2017


Article type: Communication
DOI: 10.1039/C7CC09128A
Citation: Chem. Commun., 2018,54, 662-665
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    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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