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A General and Highly Selective Palladium‐Catalyzed Hydroamidation of 1,3‐Diynes
A chemo‐, regio‐, and stereoselective mono‐hydroamidation of (un)symmetrical 1,3‐diynes is described. Key for the success of this novel transformation is the utilization of an advanced palladium catalyst system with the specific ligand Neolephos. The synthetic value of this general approach to synth...
| 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/PMC7821284/ https://www.ncbi.nlm.nih.gov/pubmed/32959449 http://dx.doi.org/10.1002/anie.202010768 |
| _version_ | 1783639389044211712 |
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| author | Liu, Jiawang Schneider, Carolin Yang, Ji Wei, Zhihong Jiao, Haijun Franke, Robert Jackstell, Ralf Beller, Matthias |
| author_facet | Liu, Jiawang Schneider, Carolin Yang, Ji Wei, Zhihong Jiao, Haijun Franke, Robert Jackstell, Ralf Beller, Matthias |
| author_sort | Liu, Jiawang |
| collection | PubMed |
| description | A chemo‐, regio‐, and stereoselective mono‐hydroamidation of (un)symmetrical 1,3‐diynes is described. Key for the success of this novel transformation is the utilization of an advanced palladium catalyst system with the specific ligand Neolephos. The synthetic value of this general approach to synthetically useful α‐alkynyl‐α, β‐unsaturated amides is showcased by diversification of several structurally complex molecules and marketed drugs. Control experiments and density‐functional theory (M06L‐SMD) computations also suggest the crucial role of the substrate in controlling the regioselectivity of unsymmetrical 1,3‐diynes. |
| format | Online Article Text |
| id | pubmed-7821284 |
| institution | National Center for Biotechnology Information |
| language | English |
| publishDate | 2020 |
| publisher | John Wiley and Sons Inc. |
| record_format | MEDLINE/PubMed |
| spelling | pubmed-78212842021-01-29 A General and Highly Selective Palladium‐Catalyzed Hydroamidation of 1,3‐Diynes Liu, Jiawang Schneider, Carolin Yang, Ji Wei, Zhihong Jiao, Haijun Franke, Robert Jackstell, Ralf Beller, Matthias Angew Chem Int Ed Engl Research Articles A chemo‐, regio‐, and stereoselective mono‐hydroamidation of (un)symmetrical 1,3‐diynes is described. Key for the success of this novel transformation is the utilization of an advanced palladium catalyst system with the specific ligand Neolephos. The synthetic value of this general approach to synthetically useful α‐alkynyl‐α, β‐unsaturated amides is showcased by diversification of several structurally complex molecules and marketed drugs. Control experiments and density‐functional theory (M06L‐SMD) computations also suggest the crucial role of the substrate in controlling the regioselectivity of unsymmetrical 1,3‐diynes. John Wiley and Sons Inc. 2020-10-27 2021-01-04 /pmc/articles/PMC7821284/ /pubmed/32959449 http://dx.doi.org/10.1002/anie.202010768 Text en © 2020 The Authors. Published by Wiley-VCH GmbH This is an open access article under the terms of the http://creativecommons.org/licenses/by-nc/4.0/ License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited and is not used for commercial purposes. |
| spellingShingle | Research Articles Liu, Jiawang Schneider, Carolin Yang, Ji Wei, Zhihong Jiao, Haijun Franke, Robert Jackstell, Ralf Beller, Matthias A General and Highly Selective Palladium‐Catalyzed Hydroamidation of 1,3‐Diynes |
| title | A General and Highly Selective Palladium‐Catalyzed Hydroamidation of 1,3‐Diynes |
| title_full | A General and Highly Selective Palladium‐Catalyzed Hydroamidation of 1,3‐Diynes |
| title_fullStr | A General and Highly Selective Palladium‐Catalyzed Hydroamidation of 1,3‐Diynes |
| title_full_unstemmed | A General and Highly Selective Palladium‐Catalyzed Hydroamidation of 1,3‐Diynes |
| title_short | A General and Highly Selective Palladium‐Catalyzed Hydroamidation of 1,3‐Diynes |
| title_sort | general and highly selective palladium‐catalyzed hydroamidation of 1,3‐diynes |
| topic | Research Articles |
| url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7821284/ https://www.ncbi.nlm.nih.gov/pubmed/32959449 http://dx.doi.org/10.1002/anie.202010768 |
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