title: 1,4-Diazabicyclo[2.2.2]octane-Promoted Aminotrifluoromethylthiolation of α,β-Unsaturated Carbonyl Compounds: N-Trifluoromethylthio-4-nitrophthalimide Acts as Both the Nitrogen and SCF3 Sources.
abstract: A novel difunctionalization reaction is described. It uses N-trifluoromethylthio-4-nitrophthalimide as the reagent, which serves as both the nitrogen and SCF3 sources. In the presence of DABCO (1,4-diazabicyclo[2.2.2]octane), the nitrogen and SCF3 groups can be incorporated into α,β-unsaturated carbonyl compounds easily and give versatile β-amino ketones and esters in good yields. This difunctionalization reaction features mild reaction conditions, high atom-economy, and efficient access to α-SCF3 amino acids.
authors.affiliation: Department of Chemistry, South University of Science and Technology of China , Shenzhen 518055, China.
authors.forename: Qing
authors.initials: Q
authors.lastname: Xiao
authors.affiliation: Department of Chemistry, South University of Science and Technology of China , Shenzhen 518055, China.
authors.forename: Qijie
authors.initials: Q
authors.lastname: He
authors.affiliation: Department of Chemistry, South University of Science and Technology of China , Shenzhen 518055, China.
authors.forename: Juncheng
authors.initials: J
authors.lastname: Li
authors.affiliation: Department of Chemistry, South University of Science and Technology of China , Shenzhen 518055, China.
authors.forename: Jun
authors.initials: J
authors.lastname: Wang
mesh_terms: D000596:Amino Acids / Q000138:chemical synthesis / Q000737:chemistry; D001372:Aza Compounds / Q000737:chemistry*; D002384:Catalysis; D034242:Cyclooctanes / Q000737:chemistry*; D008698:Mesylates / Q000737:chemistry*; D015394:Molecular Structure; D009584:Nitrogen / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000596:Amino Acids; D001372:Aza Compounds; D034242:Cyclooctanes; D008698:Mesylates; C578397:diazabicyclo(2.2.2)octane; C012077:trifluoromethanesulfonic acid; D009584:Nitrogen