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Issue 14, 2016
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Exploring structural and electronic effects in three isomers of tris{bis(trifluoromethyl)phenyl}borane: towards the combined electrochemical-frustrated Lewis pair activation of H2

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Abstract

Three structural isomers of tris{bis(trifluoromethyl)phenyl}borane have been studied as the acidic component of frustrated Lewis pairs. While the 3,5-substituted isomer is already known to heterolytically cleave H2 to generate a bridging-hydride; ortho-substituents in the 2,4- and 2,5-isomers quench such reactivity through electron donation into the vacant boron pz orbital and steric blocking of the boron centre; as shown by electrochemical, structural and computational studies. Electrochemical studies of the corresponding borohydrides identify that the two-electron oxidation of terminal-hydrides occurs at more positive potentials than observed for [HB(C6F5)3], while the bridging-hydride oxidizes at a higher potential still, comparable to that of free H2.

Graphical abstract: Exploring structural and electronic effects in three isomers of tris{bis(trifluoromethyl)phenyl}borane: towards the combined electrochemical-frustrated Lewis pair activation of H2

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Publication details

The article was received on 21 May 2015, accepted on 22 Jul 2015 and first published on 28 Jul 2015


Article type: Paper
DOI: 10.1039/C5DT01918D
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Citation: Dalton Trans., 2016,45, 6023-6031
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    Exploring structural and electronic effects in three isomers of tris{bis(trifluoromethyl)phenyl}borane: towards the combined electrochemical-frustrated Lewis pair activation of H2

    R. J. Blagg, E. J. Lawrence, K. Resner, V. S. Oganesyan, T. J. Herrington, A. E. Ashley and G. G. Wildgoose, Dalton Trans., 2016, 45, 6023
    DOI: 10.1039/C5DT01918D

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