Issue 14, 2016

Novel B(Ar′)2(Ar′′) hetero-tri(aryl)boranes: a systematic study of Lewis acidity

Abstract

A series of homo- and hetero-tri(aryl)boranes incorporating pentafluorophenyl, 3,5-bis(trifluoromethyl)phenyl, and pentachlorophenyl groups, four of which are novel species, have been studied as the acidic component of frustrated Lewis pairs for the heterolytic cleavage of H2. Under mild conditions eight of these will cleave H2; the rate of cleavage depending on both the electrophilicity of the borane and the steric bulk around the boron atom. Electrochemical studies allow comparisons of the electrophilicity with spectroscopic measurements of Lewis acidity for different series of boranes. Discrepancies in the correlation between these two types of measurements, combined with structural characterisation of each borane, reveal that the twist of the aryl rings with respect to the boron-centred trigonal plane is significant from both a steric and electronic perspective, and is an important consideration in the design of tri(aryl)boranes as Lewis acids.

Graphical abstract: Novel B(Ar′)2(Ar′′) hetero-tri(aryl)boranes: a systematic study of Lewis acidity

Supplementary files

Article information

Article type
Paper
Submitted
02 okt 2015
Accepted
28 okt 2015
First published
30 okt 2015
This article is Open Access
Creative Commons BY license

Dalton Trans., 2016,45, 6032-6043

Novel B(Ar′)2(Ar′′) hetero-tri(aryl)boranes: a systematic study of Lewis acidity

R. J. Blagg, T. R. Simmons, G. R. Hatton, J. M. Courtney, E. L. Bennett, E. J. Lawrence and G. G. Wildgoose, Dalton Trans., 2016, 45, 6032 DOI: 10.1039/C5DT03854E

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