Palladium-Catalyzed Cross-Coupling of Aryl Chlorides and Triflates with Sodium Cyanate: A Practical Synthesis of Unsymmetrical Ureas
An efficient method for palladium-catalyzed cross-coupling of aryl chlorides and triflates with sodium cyanate is reported. The protocol allows for the synthesis of unsymmetrical N,N′-di- and N,N,N′-trisubstituted ureas in one pot and is tolerant of a wide range of functional groups. Insight into th...
| Principais autores: | , , |
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| Formato: | Artigo |
| Idioma: | en_US |
| Publicado em: |
American Chemical Society (ACS)
2013
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| Acesso em linha: | http://hdl.handle.net/1721.1/81952 https://orcid.org/0000-0003-3875-4775 |
| _version_ | 1826200405720170496 |
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| author | Fors, Brett P. Vinogradova, Ekaterina Viktor Buchwald, Stephen Leffler |
| author2 | Massachusetts Institute of Technology. Department of Chemistry |
| author_facet | Massachusetts Institute of Technology. Department of Chemistry Fors, Brett P. Vinogradova, Ekaterina Viktor Buchwald, Stephen Leffler |
| author_sort | Fors, Brett P. |
| collection | MIT |
| description | An efficient method for palladium-catalyzed cross-coupling of aryl chlorides and triflates with sodium cyanate is reported. The protocol allows for the synthesis of unsymmetrical N,N′-di- and N,N,N′-trisubstituted ureas in one pot and is tolerant of a wide range of functional groups. Insight into the mechanism of aryl isocyanate formation was gleaned through studies of the transmetalation and reductive elimination steps of the reaction, including the first demonstration of reductive elimination from an arylpalladium isocyanate complex to produce an aryl isocyanate. |
| first_indexed | 2024-09-23T11:35:53Z |
| format | Article |
| id | mit-1721.1/81952 |
| institution | Massachusetts Institute of Technology |
| language | en_US |
| last_indexed | 2024-09-23T11:35:53Z |
| publishDate | 2013 |
| publisher | American Chemical Society (ACS) |
| record_format | dspace |
| spelling | mit-1721.1/819522022-09-27T20:37:26Z Palladium-Catalyzed Cross-Coupling of Aryl Chlorides and Triflates with Sodium Cyanate: A Practical Synthesis of Unsymmetrical Ureas Fors, Brett P. Vinogradova, Ekaterina Viktor Buchwald, Stephen Leffler Massachusetts Institute of Technology. Department of Chemistry Vinogradova, Ekaterina Viktor Fors, Brett P. Buchwald, Stephen Leffler An efficient method for palladium-catalyzed cross-coupling of aryl chlorides and triflates with sodium cyanate is reported. The protocol allows for the synthesis of unsymmetrical N,N′-di- and N,N,N′-trisubstituted ureas in one pot and is tolerant of a wide range of functional groups. Insight into the mechanism of aryl isocyanate formation was gleaned through studies of the transmetalation and reductive elimination steps of the reaction, including the first demonstration of reductive elimination from an arylpalladium isocyanate complex to produce an aryl isocyanate. Amgen Inc. National Institutes of Health (U.S.) (GM58160) National Science Foundation (U.S.) (Grant CHE-9808061) National Science Foundation (U.S.) (Grant DBI-9729592) National Science Foundation (U.S.) (CHE-0946721) 2013-11-01T17:30:13Z 2013-11-01T17:30:13Z 2012-06 2012-05 Article http://purl.org/eprint/type/JournalArticle 0002-7863 1520-5126 http://hdl.handle.net/1721.1/81952 Vinogradova, Ekaterina V., Brett P. Fors, and Stephen L. Buchwald. “Palladium-Catalyzed Cross-Coupling of Aryl Chlorides and Triflates with Sodium Cyanate: A Practical Synthesis of Unsymmetrical Ureas.” Journal of the American Chemical Society 134, no. 27 (July 11, 2012): 11132-11135. https://orcid.org/0000-0003-3875-4775 en_US http://dx.doi.org/10.1021/ja305212v Journal of the American Chemical Society Article is made available in accordance with the publisher's policy and may be subject to US copyright law. Please refer to the publisher's site for terms of use. application/pdf American Chemical Society (ACS) PMC |
| spellingShingle | Fors, Brett P. Vinogradova, Ekaterina Viktor Buchwald, Stephen Leffler Palladium-Catalyzed Cross-Coupling of Aryl Chlorides and Triflates with Sodium Cyanate: A Practical Synthesis of Unsymmetrical Ureas |
| title | Palladium-Catalyzed Cross-Coupling of Aryl Chlorides and Triflates with Sodium Cyanate: A Practical Synthesis of Unsymmetrical Ureas |
| title_full | Palladium-Catalyzed Cross-Coupling of Aryl Chlorides and Triflates with Sodium Cyanate: A Practical Synthesis of Unsymmetrical Ureas |
| title_fullStr | Palladium-Catalyzed Cross-Coupling of Aryl Chlorides and Triflates with Sodium Cyanate: A Practical Synthesis of Unsymmetrical Ureas |
| title_full_unstemmed | Palladium-Catalyzed Cross-Coupling of Aryl Chlorides and Triflates with Sodium Cyanate: A Practical Synthesis of Unsymmetrical Ureas |
| title_short | Palladium-Catalyzed Cross-Coupling of Aryl Chlorides and Triflates with Sodium Cyanate: A Practical Synthesis of Unsymmetrical Ureas |
| title_sort | palladium catalyzed cross coupling of aryl chlorides and triflates with sodium cyanate a practical synthesis of unsymmetrical ureas |
| url | http://hdl.handle.net/1721.1/81952 https://orcid.org/0000-0003-3875-4775 |
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