dc.contributor.author | Ambler, Brett R. | |
dc.contributor.author | Peddi, Santosh | |
dc.contributor.author | Altman, Ryan A. | |
dc.date.accessioned | 2017-03-23T16:35:40Z | |
dc.date.available | 2017-03-23T16:35:40Z | |
dc.date.issued | 2015-05-17 | |
dc.identifier.citation | Ambler, B. R., Peddi, S., & Altman, R. A. (2015). Ligand-controlled Regioselective Cu-Catalyzed Trifluoromethylation to Generate Trifluoromethylallenes. Organic Letters, 17(10), 2506–2509. http://doi.org/10.1021/acs.orglett.5b01027 | en_US |
dc.identifier.uri | http://hdl.handle.net/1808/23474 | |
dc.description.abstract | “Cu–CF3” species have been used historically for a broad spectrum of nucleophilic trifluoromethylation reactions. Although recent advancements have employed ligands to stabilize and harness the reactivity of this key organometallic intermediate, the ability of a ligand to differentiate a regiochemical outcome of a Cu–CF3-mediated or -catalyzed reaction has not been previously reported. Herein, we report the first example of a Cu-catalyzed trifluoromethylation reaction in which a ligand controls the regiochemical outcome. More specifically, we demonstrate the ability of bipyridyl-derived ligands to control the regioselectivity of the Cu-catalyzed nucleophilic trifluoromethylation reactions of propargyl electrophiles to generate trifluoromethylallenes. This method provides a variety of di-, tri- and tetra-substituted trifluoromethylallenes, which can be further modified to generate complex fluorinated substructures. | en_US |
dc.publisher | American Chemical Society | en_US |
dc.rights | This document is the Accepted Manuscript version of a Published Work that appeared in final form in Organic Letters, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see http://dx.doi.org/10.1021/acs.orglett.5b01027. | en_US |
dc.title | Ligand-controlled Regioselective Cu-Catalyzed Trifluoromethylation to Generate Trifluoromethylallenes | en_US |
dc.type | Article | en_US |
kusw.kuauthor | Ambler, Brett R. | |
kusw.kuauthor | Peddi, Santosh | |
kusw.kuauthor | Altman, Ryan A. | |
kusw.kudepartment | Chemistry | en_US |
dc.identifier.doi | 10.1021/acs.orglett.5b01027 | en_US |
kusw.oaversion | Scholarly/refereed, author accepted manuscript | en_US |
kusw.oapolicy | This item meets KU Open Access policy criteria. | en_US |
dc.rights.accessrights | openAccess | |