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Facile Protocol for Water-Tolerant “Frustrated Lewis Pair”-Catalyzed Hydrogenation

[Image: see text] Despite rapid advances in the field of metal-free, “frustrated Lewis pair” (FLP)-catalyzed hydrogenation, the need for strictly anhydrous reaction conditions has hampered wide-scale uptake of this methodology. Herein, we report that, despite the generally perceived moisture sensiti...

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Autores principales: Scott, Daniel J., Simmons, Trevor R., Lawrence, Elliot J., Wildgoose, Gregory G., Fuchter, Matthew J., Ashley, Andrew E.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2015
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4613738/
https://www.ncbi.nlm.nih.gov/pubmed/26523238
http://dx.doi.org/10.1021/acscatal.5b01417
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author Scott, Daniel J.
Simmons, Trevor R.
Lawrence, Elliot J.
Wildgoose, Gregory G.
Fuchter, Matthew J.
Ashley, Andrew E.
author_facet Scott, Daniel J.
Simmons, Trevor R.
Lawrence, Elliot J.
Wildgoose, Gregory G.
Fuchter, Matthew J.
Ashley, Andrew E.
author_sort Scott, Daniel J.
collection PubMed
description [Image: see text] Despite rapid advances in the field of metal-free, “frustrated Lewis pair” (FLP)-catalyzed hydrogenation, the need for strictly anhydrous reaction conditions has hampered wide-scale uptake of this methodology. Herein, we report that, despite the generally perceived moisture sensitivity of FLPs, 1,4-dioxane solutions of B(C(6)F(5))(3) actually show appreciable moisture tolerance and can catalyze hydrogenation of a range of weakly basic substrates without the need for rigorously inert conditions. In particular, reactions can be performed directly in commercially available nonanhydrous solvents without subsequent drying or use of internal desiccants.
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spelling pubmed-46137382015-10-28 Facile Protocol for Water-Tolerant “Frustrated Lewis Pair”-Catalyzed Hydrogenation Scott, Daniel J. Simmons, Trevor R. Lawrence, Elliot J. Wildgoose, Gregory G. Fuchter, Matthew J. Ashley, Andrew E. ACS Catal [Image: see text] Despite rapid advances in the field of metal-free, “frustrated Lewis pair” (FLP)-catalyzed hydrogenation, the need for strictly anhydrous reaction conditions has hampered wide-scale uptake of this methodology. Herein, we report that, despite the generally perceived moisture sensitivity of FLPs, 1,4-dioxane solutions of B(C(6)F(5))(3) actually show appreciable moisture tolerance and can catalyze hydrogenation of a range of weakly basic substrates without the need for rigorously inert conditions. In particular, reactions can be performed directly in commercially available nonanhydrous solvents without subsequent drying or use of internal desiccants. American Chemical Society 2015-08-17 2015-09-04 /pmc/articles/PMC4613738/ /pubmed/26523238 http://dx.doi.org/10.1021/acscatal.5b01417 Text en Copyright © 2015 American Chemical Society This is an open access article published under a Creative Commons Attribution (CC-BY) License (http://pubs.acs.org/page/policy/authorchoice_ccby_termsofuse.html) , which permits unrestricted use, distribution and reproduction in any medium, provided the author and source are cited.
spellingShingle Scott, Daniel J.
Simmons, Trevor R.
Lawrence, Elliot J.
Wildgoose, Gregory G.
Fuchter, Matthew J.
Ashley, Andrew E.
Facile Protocol for Water-Tolerant “Frustrated Lewis Pair”-Catalyzed Hydrogenation
title Facile Protocol for Water-Tolerant “Frustrated Lewis Pair”-Catalyzed Hydrogenation
title_full Facile Protocol for Water-Tolerant “Frustrated Lewis Pair”-Catalyzed Hydrogenation
title_fullStr Facile Protocol for Water-Tolerant “Frustrated Lewis Pair”-Catalyzed Hydrogenation
title_full_unstemmed Facile Protocol for Water-Tolerant “Frustrated Lewis Pair”-Catalyzed Hydrogenation
title_short Facile Protocol for Water-Tolerant “Frustrated Lewis Pair”-Catalyzed Hydrogenation
title_sort facile protocol for water-tolerant “frustrated lewis pair”-catalyzed hydrogenation
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4613738/
https://www.ncbi.nlm.nih.gov/pubmed/26523238
http://dx.doi.org/10.1021/acscatal.5b01417
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