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Molecules 2018, 23(12), 3099; https://doi.org/10.3390/molecules23123099

Exploiting the Electronic Tuneability of Carboranes as Supports for Frustrated Lewis Pairs

Institute of Chemical Sciences, School of Engineering & Physical Sciences, Heriot-Watt University, Edinburgh Scotland EH14 4AS, UK
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Academic Editor: Piotr Kaszyński
Received: 13 November 2018 / Revised: 22 November 2018 / Accepted: 23 November 2018 / Published: 27 November 2018
(This article belongs to the Special Issue Advances in Materials Derived from Polyhedral Boron Clusters)
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Abstract

The first example of a carborane with a catecholborolyl substituent, [1-Bcat-2-Ph-closo-1,2-C2B10H10] (1), has been prepared and characterized and shown to act as the Lewis acid component of an intermolecular frustrated Lewis pair in catalyzing a Michael addition. In combination with B(C6F5)3 the C-carboranylphosphine [1-PPh2-closo-1,2-C2B10H11] (IVa) is found to be comparable with PPh2(C6F5) in its ability to catalyze hydrosilylation, whilst the more strongly basic B-carboranylphosphine [9-PPh2-closo-1,7-C2B10H11] (V) is less effective and the very weakly basic species [μ-2,2′-PPh-{1-(1′-1′,2′-closo-C2B10H10)-1,2-closo-C2B10H10}] (IX) is completely ineffective. Base strengths are rank-ordered via measurement of the 1J 31P-77Se coupling constants of the phosphineselenides [1-SePPh2-closo-1,2-C2B10H11] (2), [9-SePPh2-closo-1,7-C2B10H11] (3), and [SePPh2(C6F5)] (4). View Full-Text
Keywords: carborane; phosphine; frustrated Lewis pair; catalysis carborane; phosphine; frustrated Lewis pair; catalysis
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Benton, A.; Copeland, Z.; M. Mansell, S.; M. Rosair, G.; Welch, A.J. Exploiting the Electronic Tuneability of Carboranes as Supports for Frustrated Lewis Pairs. Molecules 2018, 23, 3099.

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