Design of New Ligands for the Palladium-Catalyzed Arylation of α-Branched Secondary Amines
In Pd-catalyzed C[BOND]N cross-coupling reactions, α-branched secondary amines are difficult coupling partners and the desired products are often produced in low yields. In order to provide a robust method for accessing N-aryl α-branched tertiary amines, new catalysts have been designed to suppress...
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| Format: | Article |
| Language: | en_US |
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Wiley Blackwell
2017
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| Online Access: | http://hdl.handle.net/1721.1/110514 https://orcid.org/0000-0002-3967-2483 https://orcid.org/0000-0003-3875-4775 |
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| author | Park, Nathaniel Hamilton Vinogradova, Ekaterina V. Surry, David S Buchwald, Stephen Leffler |
| author2 | Massachusetts Institute of Technology. Department of Chemistry |
| author_facet | Massachusetts Institute of Technology. Department of Chemistry Park, Nathaniel Hamilton Vinogradova, Ekaterina V. Surry, David S Buchwald, Stephen Leffler |
| author_sort | Park, Nathaniel Hamilton |
| collection | MIT |
| description | In Pd-catalyzed C[BOND]N cross-coupling reactions, α-branched secondary amines are difficult coupling partners and the desired products are often produced in low yields. In order to provide a robust method for accessing N-aryl α-branched tertiary amines, new catalysts have been designed to suppress undesired side reactions often encountered when these amine nucleophiles are used. These advances enabled the arylation of a wide array of sterically encumbered amines, highlighting the importance of rational ligand design in facilitating challenging Pd-catalyzed cross-coupling reactions. |
| first_indexed | 2024-09-23T16:03:10Z |
| format | Article |
| id | mit-1721.1/110514 |
| institution | Massachusetts Institute of Technology |
| language | en_US |
| last_indexed | 2024-09-23T16:03:10Z |
| publishDate | 2017 |
| publisher | Wiley Blackwell |
| record_format | dspace |
| spelling | mit-1721.1/1105142022-10-02T06:01:15Z Design of New Ligands for the Palladium-Catalyzed Arylation of α-Branched Secondary Amines Park, Nathaniel Hamilton Vinogradova, Ekaterina V. Surry, David S Buchwald, Stephen Leffler Massachusetts Institute of Technology. Department of Chemistry Park, Nathaniel Hamilton Vinogradova, Ekaterina V. Surry, David S Buchwald, Stephen Leffler In Pd-catalyzed C[BOND]N cross-coupling reactions, α-branched secondary amines are difficult coupling partners and the desired products are often produced in low yields. In order to provide a robust method for accessing N-aryl α-branched tertiary amines, new catalysts have been designed to suppress undesired side reactions often encountered when these amine nucleophiles are used. These advances enabled the arylation of a wide array of sterically encumbered amines, highlighting the importance of rational ligand design in facilitating challenging Pd-catalyzed cross-coupling reactions. National Institutes of Health (U.S.) (Grant GM58160) National Science Foundation (U.S.). Graduate Research Fellowship Program 2017-07-06T20:28:08Z 2017-07-06T20:28:08Z 2015-04 2015-06 Article http://purl.org/eprint/type/JournalArticle 1433-7851 1521-3773 http://hdl.handle.net/1721.1/110514 Park, Nathaniel H. et al. “Design of New Ligands for the Palladium-Catalyzed Arylation of α-Branched Secondary Amines.” Angewandte Chemie International Edition 54.28 (2015): 8259–8262. https://orcid.org/0000-0002-3967-2483 https://orcid.org/0000-0003-3875-4775 en_US http://dx.doi.org/10.1002/anie.201502626 Angewandte Chemie International Edition Creative Commons Attribution-Noncommercial-Share Alike http://creativecommons.org/licenses/by-nc-sa/4.0/ application/pdf Wiley Blackwell PMC |
| spellingShingle | Park, Nathaniel Hamilton Vinogradova, Ekaterina V. Surry, David S Buchwald, Stephen Leffler Design of New Ligands for the Palladium-Catalyzed Arylation of α-Branched Secondary Amines |
| title | Design of New Ligands for the Palladium-Catalyzed Arylation of α-Branched Secondary Amines |
| title_full | Design of New Ligands for the Palladium-Catalyzed Arylation of α-Branched Secondary Amines |
| title_fullStr | Design of New Ligands for the Palladium-Catalyzed Arylation of α-Branched Secondary Amines |
| title_full_unstemmed | Design of New Ligands for the Palladium-Catalyzed Arylation of α-Branched Secondary Amines |
| title_short | Design of New Ligands for the Palladium-Catalyzed Arylation of α-Branched Secondary Amines |
| title_sort | design of new ligands for the palladium catalyzed arylation of α branched secondary amines |
| url | http://hdl.handle.net/1721.1/110514 https://orcid.org/0000-0002-3967-2483 https://orcid.org/0000-0003-3875-4775 |
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