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Establishing the Role of Triflate Anions in H(2) Activation by a Cationic Triorganotin(IV) Lewis Acid
[Image: see text] Cationic Lewis acids (LAs) are gaining interest as targets for frustrated Lewis pair (FLP)-mediated catalysis. Unlike neutral boranes, which are the most prevalent LAs for FLP hydrogenations, the Lewis acidity of cations can be tuned through modulation of the counteranion; however,...
Autores principales: | , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical Society
2020
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7469243/ https://www.ncbi.nlm.nih.gov/pubmed/32905389 http://dx.doi.org/10.1021/acscatal.0c02023 |
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author | Sapsford, Joshua S. Csókás, Dániel Scott, Daniel J. Turnell-Ritson, Roland C. Piascik, Adam D. Pápai, Imre Ashley, Andrew E. |
author_facet | Sapsford, Joshua S. Csókás, Dániel Scott, Daniel J. Turnell-Ritson, Roland C. Piascik, Adam D. Pápai, Imre Ashley, Andrew E. |
author_sort | Sapsford, Joshua S. |
collection | PubMed |
description | [Image: see text] Cationic Lewis acids (LAs) are gaining interest as targets for frustrated Lewis pair (FLP)-mediated catalysis. Unlike neutral boranes, which are the most prevalent LAs for FLP hydrogenations, the Lewis acidity of cations can be tuned through modulation of the counteranion; however, detailed studies on such anion effects are currently lacking in the literature. Herein, we present experimental and computational studies which probe the mechanism of H(2) activation using iPr(3)SnOTf (1-OTf) in conjunction with a coordinating (quinuclidine; qui) and noncoordinating (2,4,6-collidine; col) base and compare its reactivity with {iPr(3)Sn·base}{Al[OC(CF(3))(3)](4)} (base = qui/col) systems which lack a coordinating anion to investigate the active species responsible for H(2) activation and hence resolve any mechanistic roles for OTf(–) in the iPr(3)SnOTf-mediated pathway. |
format | Online Article Text |
id | pubmed-7469243 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2020 |
publisher | American Chemical Society |
record_format | MEDLINE/PubMed |
spelling | pubmed-74692432020-09-04 Establishing the Role of Triflate Anions in H(2) Activation by a Cationic Triorganotin(IV) Lewis Acid Sapsford, Joshua S. Csókás, Dániel Scott, Daniel J. Turnell-Ritson, Roland C. Piascik, Adam D. Pápai, Imre Ashley, Andrew E. ACS Catal [Image: see text] Cationic Lewis acids (LAs) are gaining interest as targets for frustrated Lewis pair (FLP)-mediated catalysis. Unlike neutral boranes, which are the most prevalent LAs for FLP hydrogenations, the Lewis acidity of cations can be tuned through modulation of the counteranion; however, detailed studies on such anion effects are currently lacking in the literature. Herein, we present experimental and computational studies which probe the mechanism of H(2) activation using iPr(3)SnOTf (1-OTf) in conjunction with a coordinating (quinuclidine; qui) and noncoordinating (2,4,6-collidine; col) base and compare its reactivity with {iPr(3)Sn·base}{Al[OC(CF(3))(3)](4)} (base = qui/col) systems which lack a coordinating anion to investigate the active species responsible for H(2) activation and hence resolve any mechanistic roles for OTf(–) in the iPr(3)SnOTf-mediated pathway. American Chemical Society 2020-06-08 2020-07-17 /pmc/articles/PMC7469243/ /pubmed/32905389 http://dx.doi.org/10.1021/acscatal.0c02023 Text en Copyright © 2020 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 | Sapsford, Joshua S. Csókás, Dániel Scott, Daniel J. Turnell-Ritson, Roland C. Piascik, Adam D. Pápai, Imre Ashley, Andrew E. Establishing the Role of Triflate Anions in H(2) Activation by a Cationic Triorganotin(IV) Lewis Acid |
title | Establishing the Role of Triflate Anions in H(2) Activation by a Cationic Triorganotin(IV) Lewis Acid |
title_full | Establishing the Role of Triflate Anions in H(2) Activation by a Cationic Triorganotin(IV) Lewis Acid |
title_fullStr | Establishing the Role of Triflate Anions in H(2) Activation by a Cationic Triorganotin(IV) Lewis Acid |
title_full_unstemmed | Establishing the Role of Triflate Anions in H(2) Activation by a Cationic Triorganotin(IV) Lewis Acid |
title_short | Establishing the Role of Triflate Anions in H(2) Activation by a Cationic Triorganotin(IV) Lewis Acid |
title_sort | establishing the role of triflate anions in h(2) activation by a cationic triorganotin(iv) lewis acid |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7469243/ https://www.ncbi.nlm.nih.gov/pubmed/32905389 http://dx.doi.org/10.1021/acscatal.0c02023 |
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