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The Phospha-Bora-Wittig Reaction
[Image: see text] We report the phospha-bora-Wittig reaction for the direct preparation of phosphaalkenes from aldehydes, ketones, esters, or amides. The transient phosphaborene Mes*P=B–NR(2) reacts with carbonyl compounds to form 1,2,3-phosphaboraoxetanes, analogues of oxaphosphetane intermediates...
| Autores principales: | , , , |
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| Formato: | Online Artículo Texto |
| Lenguaje: | English |
| Publicado: |
American Chemical Society
2021
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| Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8431359/ https://www.ncbi.nlm.nih.gov/pubmed/34437805 http://dx.doi.org/10.1021/jacs.1c06228 |
| _version_ | 1783750918343229440 |
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| author | Borys, Andryj M. Rice, Ella F. Nichol, Gary S. Cowley, Michael J. |
| author_facet | Borys, Andryj M. Rice, Ella F. Nichol, Gary S. Cowley, Michael J. |
| author_sort | Borys, Andryj M. |
| collection | PubMed |
| description | [Image: see text] We report the phospha-bora-Wittig reaction for the direct preparation of phosphaalkenes from aldehydes, ketones, esters, or amides. The transient phosphaborene Mes*P=B–NR(2) reacts with carbonyl compounds to form 1,2,3-phosphaboraoxetanes, analogues of oxaphosphetane intermediates in the classical Wittig reaction. 1,2,3-Phosphaboraoxetanes undergo thermal or Lewis acid-promoted cycloreversion, yielding phosphaalkenes. Experimental and density functional theory studies reveal far-reaching similarities between classical and phospha-bora-Wittig reactions. |
| format | Online Article Text |
| id | pubmed-8431359 |
| institution | National Center for Biotechnology Information |
| language | English |
| publishDate | 2021 |
| publisher | American Chemical Society |
| record_format | MEDLINE/PubMed |
| spelling | pubmed-84313592021-09-13 The Phospha-Bora-Wittig Reaction Borys, Andryj M. Rice, Ella F. Nichol, Gary S. Cowley, Michael J. J Am Chem Soc [Image: see text] We report the phospha-bora-Wittig reaction for the direct preparation of phosphaalkenes from aldehydes, ketones, esters, or amides. The transient phosphaborene Mes*P=B–NR(2) reacts with carbonyl compounds to form 1,2,3-phosphaboraoxetanes, analogues of oxaphosphetane intermediates in the classical Wittig reaction. 1,2,3-Phosphaboraoxetanes undergo thermal or Lewis acid-promoted cycloreversion, yielding phosphaalkenes. Experimental and density functional theory studies reveal far-reaching similarities between classical and phospha-bora-Wittig reactions. American Chemical Society 2021-08-26 2021-09-08 /pmc/articles/PMC8431359/ /pubmed/34437805 http://dx.doi.org/10.1021/jacs.1c06228 Text en © 2021 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by-nc-nd/4.0/Permits non-commercial access and re-use, provided that author attribution and integrity are maintained; but does not permit creation of adaptations or other derivative works (https://creativecommons.org/licenses/by-nc-nd/4.0/). |
| spellingShingle | Borys, Andryj M. Rice, Ella F. Nichol, Gary S. Cowley, Michael J. The Phospha-Bora-Wittig Reaction |
| title | The
Phospha-Bora-Wittig Reaction |
| title_full | The
Phospha-Bora-Wittig Reaction |
| title_fullStr | The
Phospha-Bora-Wittig Reaction |
| title_full_unstemmed | The
Phospha-Bora-Wittig Reaction |
| title_short | The
Phospha-Bora-Wittig Reaction |
| title_sort | the
phospha-bora-wittig reaction |
| url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8431359/ https://www.ncbi.nlm.nih.gov/pubmed/34437805 http://dx.doi.org/10.1021/jacs.1c06228 |
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