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Versatile Catalytic Hydrogenation Using A Simple Tin(IV) Lewis Acid
Author(s) -
Scott Daniel J.,
Phillips Nicholas A.,
Sapsford Joshua S.,
Deacy Arron C.,
Fuchter Matthew J.,
Ashley Andrew E.
Publication year - 2016
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201606639
Subject(s) - frustrated lewis pair , lewis acids and bases , tin , catalysis , chemistry , reactivity (psychology) , substrate (aquarium) , boron , lewis acid catalysis , combinatorial chemistry , functional group , organic chemistry , polymer chemistry , medicine , oceanography , alternative medicine , polymer , pathology , geology
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 H 2 activation and catalytic hydrogenation activity of the alternative LA iPr 3 SnOTf, which acts as a surrogate for the trialkylstannylium ion iPr 3 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.