title: Synthesis of 2-Aryl- and 2-Vinylpyrrolidines via Copper-Catalyzed Coupling of Styrenes and Dienes with Potassium β-Aminoethyl Trifluoroborates.
abstract: 2-Arylpyrrolidines occur frequently in bioactive compounds, and thus, methods to access them from readily available reagents are valuable. We report a copper-catalyzed intermolecular carboamination of vinylarenes with potassium N-carbamoyl-β-aminoethyltrifluoroborates. The reaction occurs with terminal, 1,2-disubstituted, and 1,1-disubstituted vinylarenes bearing a number of functional groups. 1,3-Dienes are also good substrates, and their reactions give 2-vinylpyrrolidines. Radical clock mechanistic experiments are consistent with the presence of carbon radical intermediates and do not support participation of carbocations.
authors.affiliation: Department of Chemistry, State University of New York at Buffalo , Buffalo, New York 14260, United States.
authors.forename: Chanchamnan
authors.initials: C
authors.lastname: Um
authors.affiliation: Department of Chemistry, State University of New York at Buffalo , Buffalo, New York 14260, United States.
authors.forename: Sherry R
authors.initials: SR
authors.lastname: Chemler
mesh_terms: D001881:Borates / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D015394:Molecular Structure; D011090:Polyenes / Q000737:chemistry*; D011759:Pyrrolidines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013343:Styrenes / Q000737:chemistry*; D014753:Vinyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D001881:Borates; D011090:Polyenes; D011759:Pyrrolidines; D013343:Styrenes; D014753:Vinyl Compounds; D003300:Copper