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Zirconium‐Catalyzed Atom‐Economical Synthesis of 1,1‐Diborylalkanes from Terminal and Internal Alkenes
A general and atom‐economical synthesis of 1,1‐diborylalkanes from alkenes and a borane without the need for an additional H(2) acceptor is reported for the first time. The key to our success is the use of an earth‐abundant zirconium‐based catalyst, which allows a balance of self‐contradictory react...
Autores principales: | , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
John Wiley and Sons Inc.
2020
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7496309/ https://www.ncbi.nlm.nih.gov/pubmed/32297413 http://dx.doi.org/10.1002/anie.202002642 |
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author | Wang, Xianjin Cui, Xin Li, Sida Wang, Yue Xia, Chungu Jiao, Haijun Wu, Lipeng |
author_facet | Wang, Xianjin Cui, Xin Li, Sida Wang, Yue Xia, Chungu Jiao, Haijun Wu, Lipeng |
author_sort | Wang, Xianjin |
collection | PubMed |
description | A general and atom‐economical synthesis of 1,1‐diborylalkanes from alkenes and a borane without the need for an additional H(2) acceptor is reported for the first time. The key to our success is the use of an earth‐abundant zirconium‐based catalyst, which allows a balance of self‐contradictory reactivities (dehydrogenative boration and hydroboration) to be achieved. Our method avoids using an excess amount of another alkene as an H(2) acceptor, which was required in other reported systems. Furthermore, substrates such as simple long‐chain aliphatic alkenes that did not react before also underwent 1,1‐diboration in our system. Significantly, the unprecedented 1,1‐diboration of internal alkenes enabled the preparation of 1,1‐diborylalkanes. |
format | Online Article Text |
id | pubmed-7496309 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2020 |
publisher | John Wiley and Sons Inc. |
record_format | MEDLINE/PubMed |
spelling | pubmed-74963092020-09-25 Zirconium‐Catalyzed Atom‐Economical Synthesis of 1,1‐Diborylalkanes from Terminal and Internal Alkenes Wang, Xianjin Cui, Xin Li, Sida Wang, Yue Xia, Chungu Jiao, Haijun Wu, Lipeng Angew Chem Int Ed Engl Communications A general and atom‐economical synthesis of 1,1‐diborylalkanes from alkenes and a borane without the need for an additional H(2) acceptor is reported for the first time. The key to our success is the use of an earth‐abundant zirconium‐based catalyst, which allows a balance of self‐contradictory reactivities (dehydrogenative boration and hydroboration) to be achieved. Our method avoids using an excess amount of another alkene as an H(2) acceptor, which was required in other reported systems. Furthermore, substrates such as simple long‐chain aliphatic alkenes that did not react before also underwent 1,1‐diboration in our system. Significantly, the unprecedented 1,1‐diboration of internal alkenes enabled the preparation of 1,1‐diborylalkanes. John Wiley and Sons Inc. 2020-05-27 2020-08-03 /pmc/articles/PMC7496309/ /pubmed/32297413 http://dx.doi.org/10.1002/anie.202002642 Text en © 2020 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 Wang, Xianjin Cui, Xin Li, Sida Wang, Yue Xia, Chungu Jiao, Haijun Wu, Lipeng Zirconium‐Catalyzed Atom‐Economical Synthesis of 1,1‐Diborylalkanes from Terminal and Internal Alkenes |
title | Zirconium‐Catalyzed Atom‐Economical Synthesis of 1,1‐Diborylalkanes from Terminal and Internal Alkenes |
title_full | Zirconium‐Catalyzed Atom‐Economical Synthesis of 1,1‐Diborylalkanes from Terminal and Internal Alkenes |
title_fullStr | Zirconium‐Catalyzed Atom‐Economical Synthesis of 1,1‐Diborylalkanes from Terminal and Internal Alkenes |
title_full_unstemmed | Zirconium‐Catalyzed Atom‐Economical Synthesis of 1,1‐Diborylalkanes from Terminal and Internal Alkenes |
title_short | Zirconium‐Catalyzed Atom‐Economical Synthesis of 1,1‐Diborylalkanes from Terminal and Internal Alkenes |
title_sort | zirconium‐catalyzed atom‐economical synthesis of 1,1‐diborylalkanes from terminal and internal alkenes |
topic | Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7496309/ https://www.ncbi.nlm.nih.gov/pubmed/32297413 http://dx.doi.org/10.1002/anie.202002642 |
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