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

Daniel Scott, Nicholas Phillips, Joshua Sapsford, Arron Deacy, Matthew J. Fuchter, Andrew Ashley

Research output: Contribution to journalArticlepeer-review

69 Citations (SciVal)

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 iPr3SnOTf, which acts as a surrogate for the trialkylstannylium ion iPr3Sn+, 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.
Original languageEnglish
Pages (from-to)4738-14742
JournalAngewandte Chemie - International Edition
Volume55
Issue number47
DOIs
Publication statusPublished - 14 Nov 2016

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