Cargando…
Magnesium Boryl Reactivity with 9‐BBN and Ph(3)B: Rational B−B′ Bond Formation and Diborane Isomerization
Reactions of a magnesium‐based pinacolatoboryl nucleophile with the electrophilic organoboranes, 9‐BBN and Ph(3)B, provide facile B−B′ single bond formation. Although the Ph(3)B derivative is thermally stable, when heated, the unsymmetrical diborane(5) anion derived from 9‐BBN is found to isomerize...
| Autores principales: | , , , |
|---|---|
| Formato: | Online Artículo Texto |
| Lenguaje: | English |
| Publicado: |
John Wiley and Sons Inc.
2017
|
| Materias: | |
| Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5767756/ https://www.ncbi.nlm.nih.gov/pubmed/29115736 http://dx.doi.org/10.1002/anie.201709902 |
| _version_ | 1783292585967616000 |
|---|---|
| author | Pécharman, Anne‐Frédérique Hill, Michael S. McMullin, Claire L. Mahon, Mary F. |
| author_facet | Pécharman, Anne‐Frédérique Hill, Michael S. McMullin, Claire L. Mahon, Mary F. |
| author_sort | Pécharman, Anne‐Frédérique |
| collection | PubMed |
| description | Reactions of a magnesium‐based pinacolatoboryl nucleophile with the electrophilic organoboranes, 9‐BBN and Ph(3)B, provide facile B−B′ single bond formation. Although the Ph(3)B derivative is thermally stable, when heated, the unsymmetrical diborane(5) anion derived from 9‐BBN is found to isomerize to two regioisomeric species via a proposed mechanism involving dehydroboration of the borabicyclo[3.3.1]nonane and syn‐diboration of the resultant alkenyl carbocycle. |
| format | Online Article Text |
| id | pubmed-5767756 |
| institution | National Center for Biotechnology Information |
| language | English |
| publishDate | 2017 |
| publisher | John Wiley and Sons Inc. |
| record_format | MEDLINE/PubMed |
| spelling | pubmed-57677562018-02-01 Magnesium Boryl Reactivity with 9‐BBN and Ph(3)B: Rational B−B′ Bond Formation and Diborane Isomerization Pécharman, Anne‐Frédérique Hill, Michael S. McMullin, Claire L. Mahon, Mary F. Angew Chem Int Ed Engl Communications Reactions of a magnesium‐based pinacolatoboryl nucleophile with the electrophilic organoboranes, 9‐BBN and Ph(3)B, provide facile B−B′ single bond formation. Although the Ph(3)B derivative is thermally stable, when heated, the unsymmetrical diborane(5) anion derived from 9‐BBN is found to isomerize to two regioisomeric species via a proposed mechanism involving dehydroboration of the borabicyclo[3.3.1]nonane and syn‐diboration of the resultant alkenyl carbocycle. John Wiley and Sons Inc. 2017-11-27 2017-12-18 /pmc/articles/PMC5767756/ /pubmed/29115736 http://dx.doi.org/10.1002/anie.201709902 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 Pécharman, Anne‐Frédérique Hill, Michael S. McMullin, Claire L. Mahon, Mary F. Magnesium Boryl Reactivity with 9‐BBN and Ph(3)B: Rational B−B′ Bond Formation and Diborane Isomerization |
| title | Magnesium Boryl Reactivity with 9‐BBN and Ph(3)B: Rational B−B′ Bond Formation and Diborane Isomerization |
| title_full | Magnesium Boryl Reactivity with 9‐BBN and Ph(3)B: Rational B−B′ Bond Formation and Diborane Isomerization |
| title_fullStr | Magnesium Boryl Reactivity with 9‐BBN and Ph(3)B: Rational B−B′ Bond Formation and Diborane Isomerization |
| title_full_unstemmed | Magnesium Boryl Reactivity with 9‐BBN and Ph(3)B: Rational B−B′ Bond Formation and Diborane Isomerization |
| title_short | Magnesium Boryl Reactivity with 9‐BBN and Ph(3)B: Rational B−B′ Bond Formation and Diborane Isomerization |
| title_sort | magnesium boryl reactivity with 9‐bbn and ph(3)b: rational b−b′ bond formation and diborane isomerization |
| topic | Communications |
| url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5767756/ https://www.ncbi.nlm.nih.gov/pubmed/29115736 http://dx.doi.org/10.1002/anie.201709902 |
| work_keys_str_mv | AT pecharmanannefrederique magnesiumborylreactivitywith9bbnandph3brationalbbbondformationanddiboraneisomerization AT hillmichaels magnesiumborylreactivitywith9bbnandph3brationalbbbondformationanddiboraneisomerization AT mcmullinclairel magnesiumborylreactivitywith9bbnandph3brationalbbbondformationanddiboraneisomerization AT mahonmaryf magnesiumborylreactivitywith9bbnandph3brationalbbbondformationanddiboraneisomerization |