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Synthesis of carbazoles

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Pschorr Reaction


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.