Issue 6, 2023

Exploration of bis(pentafluorophenyl)borinic acid as an electronically saturated, bench-top stable Lewis acid catalyst

Abstract

In efforts to develop air- and moisture-stable Lewis acid “frustrated Lewis pair” catalysts, we explored the catalytic reactivity of 9-(bis(perfluorophenyl)boraneyl)-9H-carbazole (1) towards the hydrosilylation of carbonyls. The stability of 1 was followed using nuclear magnetic resonance (NMR) spectroscopy. It was found that 1 cleanly decomposed via hydrolysis to bis(pentafluorophenyl)borinic acid (2). The borinic acid 2 was shown to be stable under ambient atmospheric conditions for upwards of 3 months in the solid-state and 2 weeks dissolved in solution. The Lewis acidity of 2 was evaluated and similarly reactivity towards hydrosilylation was observed. The use of an air-stable, inexpensive, and more sustainable silane, poly(methylhydrosiloxane) (PMHS), affords the reduction of aldehydes to alcohols under atmospheric conditions using 2, emphasizing 2 as a more sustainable, bench-top stable Lewis acid catalyst.

Graphical abstract: Exploration of bis(pentafluorophenyl)borinic acid as an electronically saturated, bench-top stable Lewis acid catalyst

Supplementary files

Article information

Article type
Paper
Submitted
03 iyl 2023
Accepted
03 avq 2023
First published
03 avq 2023
This article is Open Access
Creative Commons BY license

RSC Sustain., 2023,1, 1547-1553

Exploration of bis(pentafluorophenyl)borinic acid as an electronically saturated, bench-top stable Lewis acid catalyst

T. P. L. Cosby and C. B. Caputo, RSC Sustain., 2023, 1, 1547 DOI: 10.1039/D3SU00222E

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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