Palladium-catalyzed amination of aromatic C-H bonds with oxime esters.
We report a conceptually new approach to the direct amination of aromatic C-H bonds. In this process, an oxime ester function reacts with an aromatic C-H bond under redox-neutral conditions to form, in the case studied, an indole product. These reactions occur with relatively low catalyst loading (1 mol %) by a mechanism that appears to involve an unusual initial oxidative addition of an N-O bond to a Pd(0) species. The Pd(II) complex from oxidative addition of the N-X bond has been isolated for the first time, and evidence for the intermediacy of such oxidative addition products in the catalytic reaction has been gained.
Tan
Yichen
Y
Department of Chemistry, University of Illinois at Urbana-Champaign, 600 South Mathews Avenue, Urbana, Illinois 61801, USA.
Hartwig
John F
JF
D000586:Amination; D002244:Carbon / Q000737:chemistry*; D002384:Catalysis; D004952:Esters / Q000737:chemistry*; D006841:Hydrocarbons, Aromatic / Q000737:chemistry*; D006859:Hydrogen / Q000737:chemistry*; D007211:Indoles / Q000737:chemistry; D010091:Oximes / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*
D004952:Esters; D006841:Hydrocarbons, Aromatic; D007211:Indoles; D010091:Oximes; D010165:Palladium; D002244:Carbon; D006859:Hydrogen; C030374:indole