1417618-07-5Relevant academic research and scientific papers
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
Asymmetric oxidative coupling of hydroxycarbazoles: Facile synthesis of (+)-bi-2-hydroxy-3-methylcarbazole
Sako, Makoto,Sugizaki, Akimasa,Takizawa, Shinobu
supporting information, p. 2751 - 2753 (2018/03/05)
Asymmetric oxidative coupling reactions of hydroxycarbazoles have been established using a chiral dinuclear vanadium complex. To demonstrate the utility of vanadium-catalyzed reactions, we have used them to synthesize (+)-bi-2-hydroxy-3-carbazole in three steps from cyclohexanone and commercially available aniline derivatives.
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.
Photochemical Synthesis of Complex Carbazoles: Evaluation of Electronic Effects in Both UV- and Visible-Light Methods in Continuous Flow
Hernandez-Perez, Augusto C.,Caron, Antoine,Collins, Shawn K.
supporting information, p. 16673 - 16678 (2015/11/09)
An evaluation of both a visible-light- and UV-light-mediated synthesis of carbazoles from various triarylamines with differing electronic properties under continuous-flow conditions has been conducted. In general, triarylamines bearing electron-rich groups tend to produce higher yields than triarylamines possessing electron-withdrawing groups. The incorporation of nitrogen-based heterocycles, as well as halogen-containing arenes in carbazole skeletons, was well tolerated, and often synthetically useful complementarity was observed between the UV-light and visible-light (photoredox) methods.
Reactions of arynes with nitrosoarenes - An approach to substituted carbazoles
Chakrabarty, Shyamal,Chatterjee, Indranil,Tebben, Ludger,Studer, Armido
, p. 2968 - 2971 (2013/03/29)
No transition metals are necessary in the reaction of in situ generated arynes with nitrosoarenes to give substituted carbazoles. Depending on the fluoride source and the solvent, either N-arylated carbazoles or NH-carbazoles are obtained (see scheme; DME=dimethoxyethane, OTf=trifluoromethanesulfonate). In these cascades a C-C and one or two C-N bonds are formed. The reactions are easy to conduct and proceed under mild conditions. Copyright
