55447-28-4Relevant academic research and scientific papers
Visible-light-driven Cadogan reaction
Qu, Zhonghua,Wang, Pu,Chen, Xing,Deng, Guo-Jun,Huang, Huawen
supporting information, p. 2582 - 2586 (2021/03/09)
Visible-light-driven photochemical Cadogan-type cyclization has been discovered. The organic D-A type photosensitizer 4CzIPN found to be an efficient mediator to transfer energy from photons to the transient intermediate that breaks the barriers of deoxygenation in Cadogan reaction and enables a mild metal-free access to carbazoles and related heterocycles. DFT calculation results indicate mildly endergonic formation of the intermediate complex of nitrobiarenes and PPh3, which corresponds with experimental findings regarding reaction temperature. The robust synthetic capacity of the photoredox Cadogan reaction systems has been demonstrated by the viable productivity of a broad range of carbazoles and related N-heterocycles with good tolerance of various functionalities.
Iron-Catalyzed Intramolecular C(sp2)-H Amination
Alt, Isabel T.,Plietker, Bernd
supporting information, p. 1519 - 1522 (2016/02/14)
The nucleophilic iron complex Bu4N[Fe(CO)3(NO)] (TBA[Fe]) catalyzes the direct intramolecular C-H amination of α-azidobiaryls and (azidoaryl)alkenes into the corresponding carbazoles and indoles, respectively, under mild conditions and with low catalyst loadings. These features and the broad functional-group tolerance render this method a particularly attractive alternative to established noble-metal-based procedures.
Effect of substituted groups on the living anionic polymerization of 2-vinylcarbazole derivatives
Kang, Nam-Goo,Hur, Yoon-Hyung,Changez, Mohammad,Kang, Beom-Goo,Yu, Yong-Guen,Lee, Jae-Suk
, p. 5615 - 5625 (2013/10/21)
To study the effect of the substituents in the N-position of the carbazole on anionic polymerization, 2-vinylcarbazole derivatives of 9-butyl-2- vinylcarbazole (NBu2VCz), 9-phenyl-2-vinylcarbazole (NPh2VCz), and 9-(pyridin-2-yl)-2-vinylcarbazole (NPy2VCz) were synthesized. The anionic polymerization of NBu2VCz and NPh2VCz using s-BuLi was performed at -78 C with a 100% yield, but the polymerization of NBu2VCz showed a broader molecular weight distribution (Mw/Mn = 1.23) than NPh2VCz (M w/Mn = 1.11). The anionic polymerization of NPy2VCz using s-BuLi and DPM-K had a yield below 5%. In particular, the living anionic polymerization of NPh2VCz with s-BuLi/styrene ([s-BuLi/St]0 = 0.33) shows a narrower Mw/Mn. The block copolymerization of NPh2VCz with styrene, α-methylstyrene (α-MeSt), and 2-vinylpyridine (2VP) was achieved successfully. The resulting block copolymers of PNPh2VCz-b-P2VP with fPNPh2VCz = 17.7, 34.6, 48.1, 62.4, and 82.9 were synthesized for investigation of living characteristics.
Rh2(II)-catalyzed synthesis of carbazoles from biaryl azides
Stokes, Benjamin J.,Jovanovic, Brankica,Dong, Huijun,Richert, Kathleen J.,Riell, Ryan D.,Driver, Tom G.
supporting information; experimental part, p. 3225 - 3228 (2009/08/07)
An array of carbazoles (23 examples) can be synthesized from substituted biaryl azides at 60 °C using substoichio-metric quantities of Rh 2(O2CC3F7)4 or Rh 2(O2CC7H15)4.
