The Palladium-Catalyzed Trifluoromethylation of Vinyl Sulfonates
A method for the palladium-catalyzed trifluoromethylation of cyclohexenyl sulfonates has been developed. Various cyclohexenyl triflates and nonaflates underwent trifluoromethylation under mild reaction conditions using a catalyst system composed of Pd(dba)[subscript 2] or [(allyl)PdCl][subscript 2]...
| 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/1721.1/81967 https://orcid.org/0000-0003-3875-4775 |
| _version_ | 1826191854850277376 |
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| author | Cho, Eun Jin Buchwald, Stephen Leffler |
| author2 | Massachusetts Institute of Technology. Department of Chemistry |
| author_facet | Massachusetts Institute of Technology. Department of Chemistry Cho, Eun Jin Buchwald, Stephen Leffler |
| author_sort | Cho, Eun Jin |
| collection | MIT |
| description | A method for the palladium-catalyzed trifluoromethylation of cyclohexenyl sulfonates has been developed. Various cyclohexenyl triflates and nonaflates underwent trifluoromethylation under mild reaction conditions using a catalyst system composed of Pd(dba)[subscript 2] or [(allyl)PdCl][subscript 2] and the monodentate biaryl phosphine ligand [superscript t]BuXPhos. The trifluoromethyl anion (CF[– over 3]) or its equivalent for the process was generated in situ from TMSCF[subscript 3] in combination with KF or TESCF[subscript 3] in combination with RbF. |
| first_indexed | 2024-09-23T09:02:19Z |
| format | Article |
| id | mit-1721.1/81967 |
| institution | Massachusetts Institute of Technology |
| language | en_US |
| last_indexed | 2024-09-23T09:02:19Z |
| publishDate | 2013 |
| publisher | American Chemical Society (ACS) |
| record_format | dspace |
| spelling | mit-1721.1/819672022-09-30T12:57:47Z The Palladium-Catalyzed Trifluoromethylation of Vinyl Sulfonates Cho, Eun Jin Buchwald, Stephen Leffler Massachusetts Institute of Technology. Department of Chemistry Cho, Eun Jin Buchwald, Stephen Leffler A method for the palladium-catalyzed trifluoromethylation of cyclohexenyl sulfonates has been developed. Various cyclohexenyl triflates and nonaflates underwent trifluoromethylation under mild reaction conditions using a catalyst system composed of Pd(dba)[subscript 2] or [(allyl)PdCl][subscript 2] and the monodentate biaryl phosphine ligand [superscript t]BuXPhos. The trifluoromethyl anion (CF[– over 3]) or its equivalent for the process was generated in situ from TMSCF[subscript 3] in combination with KF or TESCF[subscript 3] in combination with RbF. National Institutes of Health (U.S.) (Grant GM46059) 2013-11-04T15:27:47Z 2013-11-04T15:27:47Z 2011-11 2011-10 Article http://purl.org/eprint/type/JournalArticle 1523-7060 1523-7052 http://hdl.handle.net/1721.1/81967 Cho, Eun Jin, and Stephen L. Buchwald. “The Palladium-Catalyzed Trifluoromethylation of Vinyl Sulfonates.” Organic Letters 13, no. 24 (December 16, 2011): 6552-6555. https://orcid.org/0000-0003-3875-4775 en_US http://dx.doi.org/10.1021/ol202885w Organic Letters 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 | Cho, Eun Jin Buchwald, Stephen Leffler The Palladium-Catalyzed Trifluoromethylation of Vinyl Sulfonates |
| title | The Palladium-Catalyzed Trifluoromethylation of Vinyl Sulfonates |
| title_full | The Palladium-Catalyzed Trifluoromethylation of Vinyl Sulfonates |
| title_fullStr | The Palladium-Catalyzed Trifluoromethylation of Vinyl Sulfonates |
| title_full_unstemmed | The Palladium-Catalyzed Trifluoromethylation of Vinyl Sulfonates |
| title_short | The Palladium-Catalyzed Trifluoromethylation of Vinyl Sulfonates |
| title_sort | palladium catalyzed trifluoromethylation of vinyl sulfonates |
| url | http://hdl.handle.net/1721.1/81967 https://orcid.org/0000-0003-3875-4775 |
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