title: Phosphine-catalyzed remote β-C-H functionalization of amines triggered by trifluoromethylation of alkenes: one-pot synthesis of bistrifluoromethylated enamides and oxazoles.
abstract: An unprecedented phosphine-catalyzed remote β-CH functionalization of amine derivatives triggered by trifluoromethylation of an alkene with Togni's reagent was disclosed. This reaction proceeded through the highly selective and concomitant activation of an unactivated alkene and the β-C sp 3H bond of an amine derivative, providing bistrifluoromethylated enamides in excellent yields with good regio-, chemo-, and stereoselectivity. Furthermore, the newly developed one-pot protocol provides a facile and step-economical access to valuable trisubstituted 5-(trifluoromethyl)oxazoles. Mechanistic studies showed that this reaction may initiate with a novel phosphine-catalyzed radical trifluoromethylation of unactivated alkene via a phosphorus radical cation.
authors.affiliation: Department of Chemistry, South University of Science and Technology of China, Shenzhen, 518055 (P.R. China).
authors.forename: Peng
authors.initials: P
authors.lastname: Yu
authors.forename: Sheng-Cai
authors.initials: SC
authors.lastname: Zheng
authors.forename: Ning-Yuan
authors.initials: NY
authors.lastname: Yang
authors.forename: Bin
authors.initials: B
authors.lastname: Tan
authors.forename: Xin-Yuan
authors.initials: XY
authors.lastname: Liu
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D000577:Amides / Q000138:chemical synthesis*; D000588:Amines / Q000737:chemistry*; D002384:Catalysis; D005465:Fluorocarbon Polymers / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D010080:Oxazoles / Q000138:chemical synthesis*; D010720:Phosphines / Q000737:chemistry*
chemical_list: D000475:Alkenes; D000577:Amides; D000588:Amines; D005465:Fluorocarbon Polymers; D007202:Indicators and Reagents; D010080:Oxazoles; D010720:Phosphines; C044646:phosphine
keywords: 1,5-H radical shift; alkenes; radical chemistry; trifluoromethylation; β-CH functionalization