title: Trifluoromethylthiolation and Trifluoromethylselenolation of α-Diazo Esters Catalyzed by Copper.
abstract: α-Diazo esters are smoothly converted into the corresponding trifluoromethyl thio- or selenoethers by reaction with Me4 NSCF3 or Me4 NSeCF3 , respectively, in the presence of catalytic amounts of copper thiocyanate. This straightforward method gives high yields under neutral conditions at room temperature and is applicable to a wide range of functionalized molecules, including diverse α-amino acid derivatives. It is well-suited for the late-stage introduction of trifluoromethylthio or -seleno groups into drug-like molecules.
authors.affiliation: FB Chemie-Organische Chemie, Technische Universität Kaiserslautern, Erwin-Schrödinger-Str. Geb. 54, 67663, Kaiserslautern, Germany.
authors.forename: Christian
authors.initials: C
authors.lastname: Matheis
authors.affiliation: FB Chemie-Organische Chemie, Technische Universität Kaiserslautern, Erwin-Schrödinger-Str. Geb. 54, 67663, Kaiserslautern, Germany.
authors.forename: Thilo
authors.initials: T
authors.lastname: Krause
authors.affiliation: FB Chemie-Organische Chemie, Technische Universität Kaiserslautern, Erwin-Schrödinger-Str. Geb. 54, 67663, Kaiserslautern, Germany.
authors.forename: Valentina
authors.initials: V
authors.lastname: Bragoni
authors.affiliation: FB Chemie-Organische Chemie, Technische Universität Kaiserslautern, Erwin-Schrödinger-Str. Geb. 54, 67663, Kaiserslautern, Germany. goossen@chemie.uni-kl.de.
authors.forename: Lukas J
authors.identifier: http://orcid.org/0000-0002-2547-3037
authors.initials: LJ
authors.lastname: Goossen
keywords: copper; diazo compounds; fluorine; fluoroalkylthiolation; synthetic methods