title: Trifluoromethylation-initiated remote cross-coupling of carbonyl compounds to form carbon-heteroatom/carbon bonds.
abstract: By involving the reversal of conventional reactivity expectations without external oxidants, we describe a novel and convenient protocol of remote cross-coupling of carbonyl compounds with a series of common and simple nucleophiles. This cross-coupling is triggered by radical trifluoromethylation of alkenes, thereby achieving highly selective remote difunctionalization of alkenes and α-position of the carbonyl group for facile access to trifluoromethyl α-halo- and α-cyanocarbonyl compounds. The reaction exhibits a broad substrate scope with excellent functionality tolerance and many different types of nucleophiles; further synthetic applicability of the obtained compounds proved to be suitable, thus showing great potential for synthetic utility.
authors.affiliation: Department of Chemistry, South University of Science and Technology of China, Shenzhen, 518055 (P. R. China).
authors.forename: Lin
authors.initials: L
authors.lastname: Huang
authors.forename: Sheng-Cai
authors.initials: SC
authors.lastname: Zheng
authors.forename: Bin
authors.initials: B
authors.lastname: Tan
authors.forename: Xin-Yuan
authors.initials: XY
authors.lastname: Liu
mesh_terms: D002244:Carbon / Q000737:chemistry*; D005617:Chlorofluorocarbons, Methane / Q000737:chemistry*; D003432:Cross-Linking Reagents / Q000737:chemistry*; D006571:Heterocyclic Compounds / Q000737:chemistry*; D008745:Methylation; D015394:Molecular Structure
chemical_list: D005617:Chlorofluorocarbons, Methane; D003432:Cross-Linking Reagents; D006571:Heterocyclic Compounds; D002244:Carbon; C009554:fluoroform
keywords: 1,5-H radical shift; CH functionalization; alkenes; cross-coupling; trifluoromethylation