Nickel-Catalyzed Heck-Type Reactions of Benzyl Chlorides and Simple Olefins
Nickel-catalyzed intermolecular benzylation and heterobenzylation of unactivated alkenes to provide functionalized allylbenzene derivatives are described. A wide range of both the benzyl chloride and alkene coupling partners are tolerated. In contrast to analogous palladium-catalyzed variants of thi...
| Main Authors: | , , |
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| Other Authors: | |
| Format: | Article |
| Language: | en_US |
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American Chemical Society (ACS)
2013
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| Online Access: | http://hdl.handle.net/1721.1/76192 https://orcid.org/0000-0002-8601-7799 |
| _version_ | 1826195955596132352 |
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| author | Matsubara, Ryosuke Gutierrez, Alicia C. Jamison, Timothy F. |
| author2 | Massachusetts Institute of Technology. Department of Chemistry |
| author_facet | Massachusetts Institute of Technology. Department of Chemistry Matsubara, Ryosuke Gutierrez, Alicia C. Jamison, Timothy F. |
| author_sort | Matsubara, Ryosuke |
| collection | MIT |
| description | Nickel-catalyzed intermolecular benzylation and heterobenzylation of unactivated alkenes to provide functionalized allylbenzene derivatives are described. A wide range of both the benzyl chloride and alkene coupling partners are tolerated. In contrast to analogous palladium-catalyzed variants of this process, all reactions described herein employ electronically unbiased aliphatic olefins (including ethylene), proceed at room temperature, and provide 1,1-disubstituted olefins over the more commonly observed 1,2-disubstituted olefins with very high selectivity. |
| first_indexed | 2024-09-23T10:18:29Z |
| format | Article |
| id | mit-1721.1/76192 |
| institution | Massachusetts Institute of Technology |
| language | en_US |
| last_indexed | 2024-09-23T10:18:29Z |
| publishDate | 2013 |
| publisher | American Chemical Society (ACS) |
| record_format | dspace |
| spelling | mit-1721.1/761922022-09-26T17:06:51Z Nickel-Catalyzed Heck-Type Reactions of Benzyl Chlorides and Simple Olefins Matsubara, Ryosuke Gutierrez, Alicia C. Jamison, Timothy F. Massachusetts Institute of Technology. Department of Chemistry Jamison, Timothy F. Matsubara, Ryosuke Gutierrez, Alicia C. Jamison, Timothy F. Nickel-catalyzed intermolecular benzylation and heterobenzylation of unactivated alkenes to provide functionalized allylbenzene derivatives are described. A wide range of both the benzyl chloride and alkene coupling partners are tolerated. In contrast to analogous palladium-catalyzed variants of this process, all reactions described herein employ electronically unbiased aliphatic olefins (including ethylene), proceed at room temperature, and provide 1,1-disubstituted olefins over the more commonly observed 1,2-disubstituted olefins with very high selectivity. 2013-01-08T16:10:07Z 2013-01-08T16:10:07Z 2011-11 2011-03 Article http://purl.org/eprint/type/JournalArticle 0002-7863 1520-5126 http://hdl.handle.net/1721.1/76192 Matsubara, Ryosuke, Alicia C. Gutierrez, and Timothy F. Jamison. “Nickel-Catalyzed Heck-Type Reactions of Benzyl Chlorides and Simple Olefins.” Journal of the American Chemical Society 133.47 (2011): 19020–19023. https://orcid.org/0000-0002-8601-7799 en_US http://dx.doi.org/ 10.1021/ja209235d 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) Prof. Jamison via Erja Kajosalo |
| spellingShingle | Matsubara, Ryosuke Gutierrez, Alicia C. Jamison, Timothy F. Nickel-Catalyzed Heck-Type Reactions of Benzyl Chlorides and Simple Olefins |
| title | Nickel-Catalyzed Heck-Type Reactions of Benzyl Chlorides and Simple Olefins |
| title_full | Nickel-Catalyzed Heck-Type Reactions of Benzyl Chlorides and Simple Olefins |
| title_fullStr | Nickel-Catalyzed Heck-Type Reactions of Benzyl Chlorides and Simple Olefins |
| title_full_unstemmed | Nickel-Catalyzed Heck-Type Reactions of Benzyl Chlorides and Simple Olefins |
| title_short | Nickel-Catalyzed Heck-Type Reactions of Benzyl Chlorides and Simple Olefins |
| title_sort | nickel catalyzed heck type reactions of benzyl chlorides and simple olefins |
| url | http://hdl.handle.net/1721.1/76192 https://orcid.org/0000-0002-8601-7799 |
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