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 11 2017
Accepted
21 12 2017
First published
21 12 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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements