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

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 s...

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Autores principales: Scott, Daniel J., Phillips, Nicholas A., Sapsford, Joshua S., Deacy, Arron C., Fuchter, Matthew J., Ashley, Andrew E.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2016
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5129554/
https://www.ncbi.nlm.nih.gov/pubmed/27774711
http://dx.doi.org/10.1002/anie.201606639
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author Scott, Daniel J.
Phillips, Nicholas A.
Sapsford, Joshua S.
Deacy, Arron C.
Fuchter, Matthew J.
Ashley, Andrew E.
author_facet Scott, Daniel J.
Phillips, Nicholas A.
Sapsford, Joshua S.
Deacy, Arron C.
Fuchter, Matthew J.
Ashley, Andrew E.
author_sort Scott, Daniel J.
collection PubMed
description 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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spelling pubmed-51295542016-11-30 Versatile Catalytic Hydrogenation Using A Simple Tin(IV) Lewis Acid Scott, Daniel J. Phillips, Nicholas A. Sapsford, Joshua S. Deacy, Arron C. Fuchter, Matthew J. Ashley, Andrew E. Angew Chem Int Ed Engl Communications 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. John Wiley and Sons Inc. 2016-10-24 2016-11-14 /pmc/articles/PMC5129554/ /pubmed/27774711 http://dx.doi.org/10.1002/anie.201606639 Text en © 2016 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution (http://creativecommons.org/licenses/by/4.0/) License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
spellingShingle Communications
Scott, Daniel J.
Phillips, Nicholas A.
Sapsford, Joshua S.
Deacy, Arron C.
Fuchter, Matthew J.
Ashley, Andrew E.
Versatile Catalytic Hydrogenation Using A Simple Tin(IV) Lewis Acid
title Versatile Catalytic Hydrogenation Using A Simple Tin(IV) Lewis Acid
title_full Versatile Catalytic Hydrogenation Using A Simple Tin(IV) Lewis Acid
title_fullStr Versatile Catalytic Hydrogenation Using A Simple Tin(IV) Lewis Acid
title_full_unstemmed Versatile Catalytic Hydrogenation Using A Simple Tin(IV) Lewis Acid
title_short Versatile Catalytic Hydrogenation Using A Simple Tin(IV) Lewis Acid
title_sort versatile catalytic hydrogenation using a simple tin(iv) lewis acid
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5129554/
https://www.ncbi.nlm.nih.gov/pubmed/27774711
http://dx.doi.org/10.1002/anie.201606639
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