dc.contributor.author | Ye, Yuxuan | |
dc.contributor.author | Takada, Takashi | |
dc.contributor.author | Buchwald, Stephen Leffler | |
dc.date.accessioned | 2018-01-10T15:57:41Z | |
dc.date.available | 2018-01-10T15:57:41Z | |
dc.date.issued | 2016-12 | |
dc.date.submitted | 2016-09 | |
dc.identifier.issn | 1433-7851 | |
dc.identifier.issn | 1521-3773 | |
dc.identifier.uri | http://hdl.handle.net/1721.1/113042 | |
dc.description.abstract | A method for the palladium-catalyzed fluorination of cyclic vinyl triflates has been developed. As with several previous palladium-catalyzed fluorination reactions using fluoride salts, controlling the regioselectivity presented a challenge in developing a practical synthetic procedure. The addition of triethyl(trifluoromethyl)silane (TESCF[subscript 3]) was found to effectively address this problem and resulted in drastically improved regioselectivities in this palladium-catalyzed fluorination reaction. This discovery, along with the use of a new biarylphosphine ligand, allowed for the development of an efficient and highly regioselective protocol for the fluorination of vinyl triflates. This method is compatible with a range of sensitive functional groups and provides access to five-, six-, and seven-membered cyclic vinyl fluorides. | en_US |
dc.description.sponsorship | National Institutes of Health (U.S.) (Grant R01GM46059) | en_US |
dc.publisher | Wiley-Blackwell | en_US |
dc.relation.isversionof | http://dx.doi.org/10.1002/ANIE.201608927 | en_US |
dc.rights | Creative Commons Attribution-Noncommercial-Share Alike | en_US |
dc.rights.uri | http://creativecommons.org/licenses/by-nc-sa/4.0/ | en_US |
dc.source | PMC | en_US |
dc.title | Palladium-Catalyzed Fluorination of Cyclic Vinyl Triflates: Effect of TESCF | en_US |
dc.type | Article | en_US |
dc.identifier.citation | Ye, Yuxuan et al. “Palladium-Catalyzed Fluorination of Cyclic Vinyl Triflates: Effect of TESCF3as an Additive.” Angewandte Chemie International Edition 55, 50 (November 2016): 15559–15563 © 2016 Wiley-VCH Verlag GmbH & Co | en_US |
dc.contributor.department | Massachusetts Institute of Technology. Department of Chemistry | en_US |
dc.contributor.mitauthor | Ye, Yuxuan | |
dc.contributor.mitauthor | Takada, Takashi | |
dc.contributor.mitauthor | Buchwald, Stephen Leffler | |
dc.relation.journal | Angewandte Chemie International Edition | en_US |
dc.eprint.version | Author's final manuscript | en_US |
dc.type.uri | http://purl.org/eprint/type/JournalArticle | en_US |
eprint.status | http://purl.org/eprint/status/PeerReviewed | en_US |
dc.date.updated | 2018-01-09T19:14:36Z | |
dspace.orderedauthors | Ye, Yuxuan; Takada, Takashi; Buchwald, Stephen L. | en_US |
dspace.embargo.terms | N | en_US |
dc.identifier.orcid | https://orcid.org/0000-0003-3516-5270 | |
dc.identifier.orcid | https://orcid.org/0000-0003-3875-4775 | |
mit.license | OPEN_ACCESS_POLICY | en_US |