- Synthesis of N-acylcarbazoles through palladium-catalyzed aryne annulation of 2-haloacetanilides
-
N-Acylcarbazoles have been synthesized in moderate to good yields by the annulation of in situ generated arynes with 2-haloacetanilides in the presence of a palladium catalyst and CsF. Both C-C and C-N bonds are formed simultaneously, and a variety of fun
- Lu, Chun,Markina, Nataliya A.,Larock, Richard C.
-
p. 11153 - 11160
(2013/02/22)
-
- Double N-arylation of primary amines: Carbazole synthesis from 2,2′-biphenyldiols
-
(Chemical Equation Presented) The double N-arylation of primary amines with 2,2′-biphenylylene ditriflates was investigated for the synthesis of multisubstituted carbazoles. Palladium complexes supported by 2-dicyclohexylphosphino-2′-methylbiphenyl or Xantphos [4,5- bis(diphenylphosphino)-9,9-dimethylxanthene] were found to be efficient catalysts for the reaction. The catalysts allow the use of anilines with an electron-donating or electron-withdrawing substituent and multisubstituted 2,2′-biphenylylene ditriflates as substrates. Ammonia equivalents, such as O-tert-butyl carbamate, are also employable as a nitrogen source to give the N-protected carbazoles which can easily give the corresponding N-unsubstituted carbazoles after deprotection. By using this methodology, a carbazole alkaloid, mukonine, is synthesized in 40% yield for five steps, in comparable efficiency to the recent precedents.
- Kuwahara, Atsushi,Nakano, Koji,Nozaki, Kyoko
-
p. 413 - 419
(2007/10/03)
-