Allenyl azide cycloaddition chemistry. photochemical initiation and CuI mediation leads to improved regioselectivity.
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.
Feldman
Ken S
KS
Department of Chemistry, The Pennsylvania State University, University Park, PA 16802, USA. ksf@chem.psu.edu
Hester
D Keith
DK
López
Carlos Silva
CS
Faza
Olalla Nieto
ON
D001386:Azides / Q000737:chemistry*; D003300:Copper / Q000737:chemistry*; D003500:Cyclization; D007454:Iodides / Q000737:chemistry*; D010777:Photochemistry
D001386:Azides; D007454:Iodides; D003300:Copper; C073870:cuprous iodide