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

Abstract

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.