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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...

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Autores principales: McLellan, Ross, Kennedy, Alan R., Orr, Samantha A., Robertson, Stuart D., Mulvey, Robert 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/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.
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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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