Oxidative Pd(II)-catalyzed C-H bond amination to carbazole at ambient temperature.
We report a new Pd(II)-catalyzed C-H bond amination reaction to form carbazoles, an important motif that is prevalent in a range of systems. The catalytic amination process operates under extremely mild conditions and produces carbazole products in good to excellent yields. Carbazoles possessing complex molecular architecture can also be formed using this reaction, highlighting its potential in natural product synthesis applications. Preliminary mechanistic investigations reveal the reaction proceeds through a Pd(II)/Pd(IV) manifold and that reductive elimination from a high oxidation state Pd(IV) complex facilitates the mild conditions of this transformation.
Jordan-Hore
James A
JA
Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge, CB2 1EW, UK.
Johansson
Carin C C
CC
Beck
Elizabeth M
EM
Gaunt
Matthew J
MJ
D000586:Amination; D002227:Carbazoles / Q000737:chemistry*; D002244:Carbon / Q000737:chemistry*; D002384:Catalysis; D006031:Glycosylation; D006859:Hydrogen / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010165:Palladium / Q000737:chemistry*; D013696:Temperature
D002227:Carbazoles; C041514:carbazole; D010165:Palladium; D002244:Carbon; D006859:Hydrogen