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Asymmetric Oxidative Coupling of Phenols and Hydroxycarbazoles
[Image: see text] The first examples of asymmetric oxidative coupling of simple phenols and 2-hydroxycarbazoles are outlined. Generation of a more vanadium catalyst by ligand design and by addition of an exogenous Brønsted or Lewis acid was found to be key to coupling the more oxidatively resistant...
| Autores principales: | , , , , , , , , , , |
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| Formato: | Online Artículo Texto |
| Lenguaje: | English |
| Publicado: |
American Chemical Society
2017
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| Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5654492/ https://www.ncbi.nlm.nih.gov/pubmed/29022352 http://dx.doi.org/10.1021/acs.orglett.7b02552 |
| _version_ | 1783273414004310016 |
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| author | Kang, Houng Lee, Young Eun Reddy, Peddiahgari Vasu Govardhana Dey, Sangeeta Allen, Scott E. Niederer, Kyle A. Sung, Paul Hewitt, Kirsten Torruellas, Carilyn Herling, Madison R. Kozlowski, Marisa C. |
| author_facet | Kang, Houng Lee, Young Eun Reddy, Peddiahgari Vasu Govardhana Dey, Sangeeta Allen, Scott E. Niederer, Kyle A. Sung, Paul Hewitt, Kirsten Torruellas, Carilyn Herling, Madison R. Kozlowski, Marisa C. |
| author_sort | Kang, Houng |
| collection | PubMed |
| description | [Image: see text] The first examples of asymmetric oxidative coupling of simple phenols and 2-hydroxycarbazoles are outlined. Generation of a more vanadium catalyst by ligand design and by addition of an exogenous Brønsted or Lewis acid was found to be key to coupling the more oxidatively resistant phenols. The resultant vanadium complex is both more Lewis acidic and more strongly oxidizing. Good to excellent levels of enantioselectivity could be obtained, and simple trituration readily provided the products with ≥95% ee. |
| format | Online Article Text |
| id | pubmed-5654492 |
| institution | National Center for Biotechnology Information |
| language | English |
| publishDate | 2017 |
| publisher | American Chemical Society |
| record_format | MEDLINE/PubMed |
| spelling | pubmed-56544922018-10-12 Asymmetric Oxidative Coupling of Phenols and Hydroxycarbazoles Kang, Houng Lee, Young Eun Reddy, Peddiahgari Vasu Govardhana Dey, Sangeeta Allen, Scott E. Niederer, Kyle A. Sung, Paul Hewitt, Kirsten Torruellas, Carilyn Herling, Madison R. Kozlowski, Marisa C. Org Lett [Image: see text] The first examples of asymmetric oxidative coupling of simple phenols and 2-hydroxycarbazoles are outlined. Generation of a more vanadium catalyst by ligand design and by addition of an exogenous Brønsted or Lewis acid was found to be key to coupling the more oxidatively resistant phenols. The resultant vanadium complex is both more Lewis acidic and more strongly oxidizing. Good to excellent levels of enantioselectivity could be obtained, and simple trituration readily provided the products with ≥95% ee. American Chemical Society 2017-10-12 2017-10-20 /pmc/articles/PMC5654492/ /pubmed/29022352 http://dx.doi.org/10.1021/acs.orglett.7b02552 Text en Copyright © 2017 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes. |
| spellingShingle | Kang, Houng Lee, Young Eun Reddy, Peddiahgari Vasu Govardhana Dey, Sangeeta Allen, Scott E. Niederer, Kyle A. Sung, Paul Hewitt, Kirsten Torruellas, Carilyn Herling, Madison R. Kozlowski, Marisa C. Asymmetric Oxidative Coupling of Phenols and Hydroxycarbazoles |
| title | Asymmetric Oxidative Coupling of Phenols and Hydroxycarbazoles |
| title_full | Asymmetric Oxidative Coupling of Phenols and Hydroxycarbazoles |
| title_fullStr | Asymmetric Oxidative Coupling of Phenols and Hydroxycarbazoles |
| title_full_unstemmed | Asymmetric Oxidative Coupling of Phenols and Hydroxycarbazoles |
| title_short | Asymmetric Oxidative Coupling of Phenols and Hydroxycarbazoles |
| title_sort | asymmetric oxidative coupling of phenols and hydroxycarbazoles |
| url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5654492/ https://www.ncbi.nlm.nih.gov/pubmed/29022352 http://dx.doi.org/10.1021/acs.orglett.7b02552 |
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