Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 55, Issue 47, Pages 14738-14742Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201606639
Keywords
catalysis; frustrated Lewis pairs; hydrogenation; stannylium; tin
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Funding
- GreenCatEng
- Eli Lilly (Pharmacat consortium)
- EPSRC
- Royal Society
- Engineering and Physical Sciences Research Council [1376417] Funding Source: researchfish
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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.
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