Direct Reductive Amination of Carbonyl Compounds Catalyzed by a Moisture Tolerant Tin(IV) Lewis Acid

Despite the ever‐broadening applications of main‐group ‘frustrated Lewis pair’ (FLP) chemistry to both new and established reactions, their typical intolerance of water, especially at elevated temperatures (>100 °C), represents a key barrier to their mainstream adoption. Herein we report that FLP...

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Autores principales: Sapsford, Joshua S., Scott, Daniel J., Allcock, Nathan J., Fuchter, Matthew J., Tighe, Christopher J., Ashley, Andrew E.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2018
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5901005/
https://www.ncbi.nlm.nih.gov/pubmed/29706853
http://dx.doi.org/10.1002/adsc.201701418
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author Sapsford, Joshua S.
Scott, Daniel J.
Allcock, Nathan J.
Fuchter, Matthew J.
Tighe, Christopher J.
Ashley, Andrew E.
author_facet Sapsford, Joshua S.
Scott, Daniel J.
Allcock, Nathan J.
Fuchter, Matthew J.
Tighe, Christopher J.
Ashley, Andrew E.
author_sort Sapsford, Joshua S.
collection PubMed
description Despite the ever‐broadening applications of main‐group ‘frustrated Lewis pair’ (FLP) chemistry to both new and established reactions, their typical intolerance of water, especially at elevated temperatures (>100 °C), represents a key barrier to their mainstream adoption. Herein we report that FLPs based on the Lewis acid (i)Pr(3)SnOTf are moisture tolerant in the presence of moderately strong nitrogenous bases, even under high temperature regimes, allowing them to operate as simple and effective catalysts for the reductive amination of organic carbonyls, including for challenging bulky amine and carbonyl substrate partners. [Image: see text]
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spelling pubmed-59010052018-04-24 Direct Reductive Amination of Carbonyl Compounds Catalyzed by a Moisture Tolerant Tin(IV) Lewis Acid Sapsford, Joshua S. Scott, Daniel J. Allcock, Nathan J. Fuchter, Matthew J. Tighe, Christopher J. Ashley, Andrew E. Adv Synth Catal Communications Despite the ever‐broadening applications of main‐group ‘frustrated Lewis pair’ (FLP) chemistry to both new and established reactions, their typical intolerance of water, especially at elevated temperatures (>100 °C), represents a key barrier to their mainstream adoption. Herein we report that FLPs based on the Lewis acid (i)Pr(3)SnOTf are moisture tolerant in the presence of moderately strong nitrogenous bases, even under high temperature regimes, allowing them to operate as simple and effective catalysts for the reductive amination of organic carbonyls, including for challenging bulky amine and carbonyl substrate partners. [Image: see text] John Wiley and Sons Inc. 2018-01-15 2018-03-20 /pmc/articles/PMC5901005/ /pubmed/29706853 http://dx.doi.org/10.1002/adsc.201701418 Text en © 2018 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the 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
Sapsford, Joshua S.
Scott, Daniel J.
Allcock, Nathan J.
Fuchter, Matthew J.
Tighe, Christopher J.
Ashley, Andrew E.
Direct Reductive Amination of Carbonyl Compounds Catalyzed by a Moisture Tolerant Tin(IV) Lewis Acid
title Direct Reductive Amination of Carbonyl Compounds Catalyzed by a Moisture Tolerant Tin(IV) Lewis Acid
title_full Direct Reductive Amination of Carbonyl Compounds Catalyzed by a Moisture Tolerant Tin(IV) Lewis Acid
title_fullStr Direct Reductive Amination of Carbonyl Compounds Catalyzed by a Moisture Tolerant Tin(IV) Lewis Acid
title_full_unstemmed Direct Reductive Amination of Carbonyl Compounds Catalyzed by a Moisture Tolerant Tin(IV) Lewis Acid
title_short Direct Reductive Amination of Carbonyl Compounds Catalyzed by a Moisture Tolerant Tin(IV) Lewis Acid
title_sort direct reductive amination of carbonyl compounds catalyzed by a moisture tolerant tin(iv) lewis acid
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5901005/
https://www.ncbi.nlm.nih.gov/pubmed/29706853
http://dx.doi.org/10.1002/adsc.201701418
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