1417618-07-5Relevant articles and documents
A visible-light-mediated synthesis of carbazoles
Hernandez-Perez, Augusto C.,Collins, Shawn K.
, p. 12696 - 12700 (2013)
The photosynthetic preparation of N-aryl- and N-alkyl-bearing carbazoles utilizes continuous flow, visible light, and an in situ formed Cu-based sensitizer (see picture). The method is mild and efficient, and allows the straightforward synthesis of a variety of carbazoles with different substituents, heterocycles, and complex carbon architectures. Copyright
Photochemical Synthesis of Carbazoles Using an [Fe(phen)3](NTf2)2/O2 Catalyst System: Catalysis toward Sustainability
Parisien-Collette, Shawn,Hernandez-Perez, Augusto C.,Collins, Shawn K.
supporting information, p. 4994 - 4997 (2016/10/14)
An increasingly sustainable photochemical synthesis of carbazoles was developed using a catalytic system of Fe(phen)3(NTf2)2/O2 under continuous flow conditions and was demonstrated on gram-scale using a numbering-up strategy. Photocyclization of triaryl and diarylamines into the corresponding carbazoles occurs in general in higher yields than with previously developed photocatalysts.
"transition-metal-free" synthesis of carbazoles by photostimulated reactions of 2′-halo[1,1′-biphenyl]-2-amines
Guerra, Walter D.,Rossi, Roberto A.,Pierini, Adriana B.,Barolo, Silvia M.
, p. 928 - 941 (2015/01/30)
An efficient and simple protocol for the preparation of a series of 9H-carbazoles by photostimulated SRN1 substitution reactions is presented. Substituted 9H-carbazoles were synthesized in low to excellent yields (up to 96%) through an intramolecular C-N bond formation of 2′-halo[1,1′-biphenyl]-2-amines by the photoinitiated SRN1 mechanism under mild and "transition-metal-free" conditions. The biphenylamines used as substrates were obtained with isolated yields ranging from 21% to 84% by two approaches: (A) the cross-coupling Suzuki-Miyaura reaction and (B) the radical arylation of anilines. Some key aspects of the proposed mechanism were evaluated at the B3LYP/6-311+G? level.
