Issue 14, 2016

Pyridinium–phosphonium dications: highly electrophilic phosphorus-based Lewis acid catalysts

Abstract

Using commercially available 2-pyridyldiphenylphosphine (o-NC5H4)PPh2, a family of electrophilic phosphonium cations [(o-NC5H4)PFPh2]+ (2) and dications [(o-MeNC5H4)PRPh2]2+ (R = F (4); Me (5)) were prepared. The Lewis acidity of these pyridinium–phosphonium dications was probed in Friedel–Crafts dimerization, hydrodefluorination, hydrosilylation, dehydrocoupling and hydrodeoxygenation reactions. The influence of the counterion on the catalytic activity of the electrophilic phosphonium cations is also discussed.

Graphical abstract: Pyridinium–phosphonium dications: highly electrophilic phosphorus-based Lewis acid catalysts

Supplementary files

Article information

Article type
Paper
Submitted
29 Sep 2015
Accepted
30 Nov 2015
First published
07 Des 2015

Dalton Trans., 2016,45, 5949-5957

Author version available

Pyridinium–phosphonium dications: highly electrophilic phosphorus-based Lewis acid catalysts

J. M. Bayne, M. H. Holthausen and D. W. Stephan, Dalton Trans., 2016, 45, 5949 DOI: 10.1039/C5DT03796D

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