Isoquinoline synthesis via rhodium-catalyzed oxidative cross-coupling/cyclization of aryl aldimines and alkynes.
A general rhodium-catalyzed oxidative coupling reaction between internal alkynes and aryl aldimines is described. This process affords 3,4-disubstituted isoquinolines in good yield and high regioselectivity. Preliminary mechanistic studies suggest that the C-N bond formation arises from the reductive elimination of a rhodium(III) species.
Guimond
Nicolas
N
Centre for Catalysis Research and Innovation, Department of Chemistry, University of Ottawa, 10 Marie Curie, Ottawa, Canada K1N 6N5.
Fagnou
Keith
K
D000480:Alkynes / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D007097:Imines / Q000737:chemistry*; D007546:Isoquinolines / Q000138:chemical synthesis* / Q000737:chemistry; D010084:Oxidation-Reduction; D012238:Rhodium / Q000737:chemistry*
D000480:Alkynes; D007097:Imines; D007546:Isoquinolines; D012238:Rhodium; C039109:isoquinoline