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. 2017 Aug 28;375(2101):20170008.
doi: 10.1098/rsta.2017.0008.

Hydrogen activation using a novel tribenzyltin Lewis acid

Robert T Cooper  1 , Joshua S Sapsford  1 , Roland C Turnell-Ritson  1 , Dong-Hun Hyon  1 , Andrew J P White  1 , Andrew E Ashley  2
Affiliations

Hydrogen activation using a novel tribenzyltin Lewis acid

Robert T Cooper et al. Philos Trans A Math Phys Eng Sci. .

Abstract

Over the last decade there has been an explosion in the reactivity and applications of frustrated Lewis pair (FLP) chemistry. Despite this, the Lewis acids (LAs) in these transformations are often boranes, with heavier p-block elements receiving surprisingly little attention. The novel LA Bn3SnOTf (1) has been synthesized from simple, inexpensive starting materials and has been spectroscopically and structurally characterized. Subtle modulation of the electronics at the tin centre has led to an increase in its Lewis acidity in comparison with previously reported R3SnOTf LAs, and has facilitated low temperature hydrogen activation and imine hydrogenation. Deactivation pathways of the R3Sn+ LA core have also been investigated.This article is part of the themed issue 'Frustrated Lewis pair chemistry'.

Keywords: Lewis acids; frustrated Lewis pairs; hydrogen activation; hydrogenation; tin.

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Conflict of interest statement

We declare we have no competing interests.

Figures

Figure 1.
Figure 1.
Synthesis of 1.
Figure 2.
Figure 2.
Molecular structure of 1 (molecule a). Ellipsoids shown at 50% probability, H atoms omitted for clarity (C atoms blue, O atoms red, F atoms green, S atoms yellow, Sn atoms pink). (a) View of one independent Bn3SnOTf fragment in the asymmetric unit. (b) Extended view of the polymeric structure generated from the independent fragment along the b axis (all four independent molecules form similar polymeric chains).
Figure 3.
Figure 3.
1H NMR spectra of 1 and collidine in C6D6 before (a) and after (b) admission of H2 (4 bar). Insets show Sn-H resonance and 1J(117/119Sn-1H) satellites.
Figure 4.
Figure 4.
(a,b) Proposed deactivation pathways for Bn3SnX (X = TfO, H; 1, 2) during H2 heterolysis reactions.
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