Negishi Coupling of Secondary Alkylzinc Halides with Aryl Bromides and Chlorides
An efficient palladium-catalyzed process has been developed for Negishi coupling of secondary alkylzinc halides with a wide range of aryl bromides and activated aryl chlorides. A palladium catalyst composed of a new biaryldialkylphosphine ligand, CPhos, effectively promotes the rate of the reductive...
| 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/1721.1/82067 https://orcid.org/0000-0003-3875-4775 |
| _version_ | 1811091083928535040 |
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| author | Han, Chong Buchwald, Stephen Leffler |
| author2 | Massachusetts Institute of Technology. Department of Chemistry |
| author_facet | Massachusetts Institute of Technology. Department of Chemistry Han, Chong Buchwald, Stephen Leffler |
| author_sort | Han, Chong |
| collection | MIT |
| description | An efficient palladium-catalyzed process has been developed for Negishi coupling of secondary alkylzinc halides with a wide range of aryl bromides and activated aryl chlorides. A palladium catalyst composed of a new biaryldialkylphosphine ligand, CPhos, effectively promotes the rate of the reductive elimination step relative to the rate of the undesired β-hydride elimination. The broad substrate scope and excellent ratio of the desired secondary to the undesired primary coupling product make this method a powerful and reliable tool for C(sp[superscript 3])−C(sp[superscript 2]) bond formation. |
| first_indexed | 2024-09-23T14:56:46Z |
| format | Article |
| id | mit-1721.1/82067 |
| institution | Massachusetts Institute of Technology |
| language | en_US |
| last_indexed | 2024-09-23T14:56:46Z |
| publishDate | 2013 |
| publisher | American Chemical Society (ACS) |
| record_format | dspace |
| spelling | mit-1721.1/820672022-09-29T11:33:22Z Negishi Coupling of Secondary Alkylzinc Halides with Aryl Bromides and Chlorides Han, Chong Buchwald, Stephen Leffler Massachusetts Institute of Technology. Department of Chemistry Han, Chong Buchwald, Stephen Leffler An efficient palladium-catalyzed process has been developed for Negishi coupling of secondary alkylzinc halides with a wide range of aryl bromides and activated aryl chlorides. A palladium catalyst composed of a new biaryldialkylphosphine ligand, CPhos, effectively promotes the rate of the reductive elimination step relative to the rate of the undesired β-hydride elimination. The broad substrate scope and excellent ratio of the desired secondary to the undesired primary coupling product make this method a powerful and reliable tool for C(sp[superscript 3])−C(sp[superscript 2]) bond formation. National Institutes of Health (U.S.) (GM 46059) National Institutes of Health (U.S.) (GM 1S10RR13886-01) 2013-11-08T20:33:30Z 2013-11-08T20:33:30Z 2009-05 2009-03 Article http://purl.org/eprint/type/JournalArticle 0002-7863 1520-5126 http://hdl.handle.net/1721.1/82067 Han, Chong, and Stephen L. Buchwald. “Negishi Coupling of Secondary Alkylzinc Halides with Aryl Bromides and Chlorides.” Journal of the American Chemical Society 131, no. 22 (June 10, 2009): 7532-7533. https://orcid.org/0000-0003-3875-4775 en_US http://dx.doi.org/10.1021/ja902046m 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 | Han, Chong Buchwald, Stephen Leffler Negishi Coupling of Secondary Alkylzinc Halides with Aryl Bromides and Chlorides |
| title | Negishi Coupling of Secondary Alkylzinc Halides with Aryl Bromides and Chlorides |
| title_full | Negishi Coupling of Secondary Alkylzinc Halides with Aryl Bromides and Chlorides |
| title_fullStr | Negishi Coupling of Secondary Alkylzinc Halides with Aryl Bromides and Chlorides |
| title_full_unstemmed | Negishi Coupling of Secondary Alkylzinc Halides with Aryl Bromides and Chlorides |
| title_short | Negishi Coupling of Secondary Alkylzinc Halides with Aryl Bromides and Chlorides |
| title_sort | negishi coupling of secondary alkylzinc halides with aryl bromides and chlorides |
| url | http://hdl.handle.net/1721.1/82067 https://orcid.org/0000-0003-3875-4775 |
| work_keys_str_mv | AT hanchong negishicouplingofsecondaryalkylzinchalideswitharylbromidesandchlorides AT buchwaldstephenleffler negishicouplingofsecondaryalkylzinchalideswitharylbromidesandchlorides |