Categories: Synthesis of N-Heterocycles >
Synthesis of carbazoles
Name Reactions
Recent Literature
A palladium-catalyzed tandem directed C-H
functionalization and amide arylation gave a series of substituted carbazoles. The Pd(0) species
generated are reoxidized to Pd(II) in the presence of Cu(OAc)2 and an atmosphere
of oxygen.
W. C. P. Tsang, N. Zheng, S. L. Buchwald, J. Am. Chem. Soc.,
2005, 127, 14560-14561.
An intramolecular palladium(II)-catalyzed oxidative carbon-carbon bond formation
under air in the presence of pivalic acid as the reaction solvent, instead of
acetic acid, results in greater reproducibility, higher yields, and broader
substrate scope. The reaction allows the conversion of both electron-rich and
electron-deficient diarylamines.
B. Liégault, D. Lee, M. P. Huestis, D. R. Stuart, K. Fagnou, J. Org. Chem., 2008,
73, 5022-5028.
An efficient route to carbazoles and dibenzofurans has
been developed. The reaction of
o-iodoanilines or o-iodophenols with silylaryl triflates in the
presence of CsF to afford N- or O-arylated products is followed by
a cyclization using a Pd catalyst to carbazoles and dibenzofurans in good to
excellent yields. Various functional groups are tolerated.
Z. Liu, R. C. Larock, Org. Lett., 2004, 6, 3739-3741.
