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. 2016 Nov 14;55(47):14738-14742.
doi: 10.1002/anie.201606639. Epub 2016 Oct 24.

Versatile Catalytic Hydrogenation Using A Simple Tin(IV) Lewis Acid

Daniel J Scott  1 , Nicholas A Phillips  1 , Joshua S Sapsford  1 , Arron C Deacy  1 , Matthew J Fuchter  1 , Andrew E Ashley  1
Affiliations

Versatile Catalytic Hydrogenation Using A Simple Tin(IV) Lewis Acid

Daniel J Scott et al. Angew Chem Int Ed Engl. .

Abstract

Despite the rapid development of frustrated Lewis pair (FLP) chemistry over the last ten years, its application in catalytic hydrogenations remains dependent on a narrow family of structurally similar early main-group Lewis acids (LAs), inevitably placing limitations on reactivity, sensitivity and substrate scope. Herein we describe the FLP-mediated H2 activation and catalytic hydrogenation activity of the alternative LA iPr3 SnOTf, which acts as a surrogate for the trialkylstannylium ion iPr3 Sn+ , and is rapidly and easily prepared from simple, inexpensive starting materials. This highly thermally robust LA is found to be competent in the hydrogenation of a number of different unsaturated functional groups (which is unique to date for main-group FLP LAs not based on boron), and also displays a remarkable tolerance to moisture.

Keywords: catalysis; frustrated Lewis pairs; hydrogenation; stannylium; tin.

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Figures

Scheme 1
Scheme 1
Synthesis of [1]OTf.
Scheme 2
Scheme 2
a) Proposed mechanism for catalytic hydrogenation of 4 a using [1]OTf ([N]=2,4,6‐collidine) and b) alternative H2 activation using in situ generated [1]OiPr.
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