title: Allenyl azide cycloaddition chemistry. photochemical initiation and CuI mediation leads to improved regioselectivity.
abstract: Irradiation of 2-(3-alkenyl)allenylphenyl azides in the presence of excess CuI furnished functionalized 2,3-cyclopentenylindoles in good yield with only trace amounts of competitive C-N-bonded regioisomeric products. These results represent a significant departure from the modest-to-nonexistent regioselectivity that attended thermal cyclization of these allenyl azide substrates.
authors.affiliation: Department of Chemistry, The Pennsylvania State University, University Park, PA 16802, USA. ksf@chem.psu.edu
authors.forename: Ken S
authors.initials: KS
authors.lastname: Feldman
authors.forename: D Keith
authors.initials: DK
authors.lastname: Hester
authors.forename: Carlos Silva
authors.initials: CS
authors.lastname: López
authors.forename: Olalla Nieto
authors.initials: ON
authors.lastname: Faza
mesh_terms: D001386:Azides / Q000737:chemistry*; D003300:Copper / Q000737:chemistry*; D003500:Cyclization; D007454:Iodides / Q000737:chemistry*; D010777:Photochemistry
chemical_list: D001386:Azides; D007454:Iodides; D003300:Copper; C073870:cuprous iodide