Combined C-H functionalization/C-N bond formation route to carbazoles.
A new method in which a series of substituted carbazoles is efficiently produced by the combination of an amide and an arene is described. The key feature of this method is the palladium-catalyzed tandem directed C-H functionalization and amide arylation. The method tolerates substitution on either ring of the biaryl amide substrates, and the products can be assembled in a simple two-step protocol from readily available reagents. The Pd(0) species generated are reoxidized to Pd(II) in the presence of Cu(OAc)2 and an atmosphere of oxygen.
Tsang
W C Peter
WC
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA.
Zheng
Nan
N
Buchwald
Stephen L
SL
D002227:Carbazoles / Q000138:chemical synthesis* / Q000737:chemistry; D002244:Carbon / Q000737:chemistry*; D003500:Cyclization; D006859:Hydrogen / Q000737:chemistry*; D015394:Molecular Structure; D009584:Nitrogen / Q000737:chemistry*
D002227:Carbazoles; D002244:Carbon; D006859:Hydrogen; D009584:Nitrogen