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Lithium Dihydropyridine Dehydrogenation Catalysis: A Group 1 Approach to the Cyclization of Diamine Boranes
In reactions restricted previously to a ruthenium catalyst, a 1‐lithium‐2‐alkyl‐1,2‐dihydropyridine complex is shown to be a competitive alternative dehydrogenation catalyst for the transformation of diamine boranes into cyclic 1,3,2‐diazaborolidines, which can in turn be smoothly arylated in good y...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
John Wiley and Sons Inc.
2016
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5396369/ https://www.ncbi.nlm.nih.gov/pubmed/28000994 http://dx.doi.org/10.1002/anie.201610905 |
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author | McLellan, Ross Kennedy, Alan R. Orr, Samantha A. Robertson, Stuart D. Mulvey, Robert E. |
author_facet | McLellan, Ross Kennedy, Alan R. Orr, Samantha A. Robertson, Stuart D. Mulvey, Robert E. |
author_sort | McLellan, Ross |
collection | PubMed |
description | In reactions restricted previously to a ruthenium catalyst, a 1‐lithium‐2‐alkyl‐1,2‐dihydropyridine complex is shown to be a competitive alternative dehydrogenation catalyst for the transformation of diamine boranes into cyclic 1,3,2‐diazaborolidines, which can in turn be smoothly arylated in good yields. This study established the conditions and solvent dependence of the catalysis through NMR monitoring, with mechanistic insight provided by NMR (including DOSY) experiments and X‐ray crystallographic studies of several model lithio intermediates. |
format | Online Article Text |
id | pubmed-5396369 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2016 |
publisher | John Wiley and Sons Inc. |
record_format | MEDLINE/PubMed |
spelling | pubmed-53963692017-05-04 Lithium Dihydropyridine Dehydrogenation Catalysis: A Group 1 Approach to the Cyclization of Diamine Boranes McLellan, Ross Kennedy, Alan R. Orr, Samantha A. Robertson, Stuart D. Mulvey, Robert E. Angew Chem Int Ed Engl Communications In reactions restricted previously to a ruthenium catalyst, a 1‐lithium‐2‐alkyl‐1,2‐dihydropyridine complex is shown to be a competitive alternative dehydrogenation catalyst for the transformation of diamine boranes into cyclic 1,3,2‐diazaborolidines, which can in turn be smoothly arylated in good yields. This study established the conditions and solvent dependence of the catalysis through NMR monitoring, with mechanistic insight provided by NMR (including DOSY) experiments and X‐ray crystallographic studies of several model lithio intermediates. John Wiley and Sons Inc. 2016-12-21 2017-01-19 /pmc/articles/PMC5396369/ /pubmed/28000994 http://dx.doi.org/10.1002/anie.201610905 Text en © 2017 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 McLellan, Ross Kennedy, Alan R. Orr, Samantha A. Robertson, Stuart D. Mulvey, Robert E. Lithium Dihydropyridine Dehydrogenation Catalysis: A Group 1 Approach to the Cyclization of Diamine Boranes |
title | Lithium Dihydropyridine Dehydrogenation Catalysis: A Group 1 Approach to the Cyclization of Diamine Boranes |
title_full | Lithium Dihydropyridine Dehydrogenation Catalysis: A Group 1 Approach to the Cyclization of Diamine Boranes |
title_fullStr | Lithium Dihydropyridine Dehydrogenation Catalysis: A Group 1 Approach to the Cyclization of Diamine Boranes |
title_full_unstemmed | Lithium Dihydropyridine Dehydrogenation Catalysis: A Group 1 Approach to the Cyclization of Diamine Boranes |
title_short | Lithium Dihydropyridine Dehydrogenation Catalysis: A Group 1 Approach to the Cyclization of Diamine Boranes |
title_sort | lithium dihydropyridine dehydrogenation catalysis: a group 1 approach to the cyclization of diamine boranes |
topic | Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5396369/ https://www.ncbi.nlm.nih.gov/pubmed/28000994 http://dx.doi.org/10.1002/anie.201610905 |
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