1392423-09-4Relevant articles and documents
Transition-Metal-Controlled Synthesis of 11 H-Benzo[ a]carbazoles and 6-Alkylidene-6 H-isoindo[2,1- a]indoles via Sequential Intermolecular/Intramolecular Cross-Dehydrogenative Coupling from 2-Phenylindoles
Liu, Anyi,Han, Qingshuai,Zhang, Xiaofeng,Li, Buhong,Huang, Qiufeng
, p. 6839 - 6843 (2019)
A catalyst-controlled synthesis of 11H-benzo[a]carbazoles and 6-alkylidene-6H-isoindo[2,1-a]indoles is described. Pd(OAc)2 favored 6-alkylidene-6H-isoindo[2,1-a]indoles via intramolecular C-H/N-H CDC reaction, while [CpRhCl2]2/
Selective Synthesis of Benzo[a]Carbazoles and Indolo[2,1-a]-Isoquinolines via Rh(III)-Catalyzed C?H Functionalizations of 2-Arylindoles with Sulfoxonium Ylides
Chen, Guang,Zhang, Xinying,Jia, Ruixue,Li, Bin,Fan, Xuesen
supporting information, p. 3781 - 3787 (2018/09/20)
A highly chem- and regioselective synthesis of diversely substituted benzo[a]carbazoles and indolo[2,1-a]-isoquinolines through Rh(III)-catalyzed cascade reactions of 2-arylindoles with sulfoxonium ylides is presented. To be specific, treatment of 2-arylindoles, 2-arylindole-3-carbaldehydes, 2-arylindole-3-carbonitriles or 2-aryl-3-methylindoles with sulfoxonium ylides under the catalysis of Rh(III) led to the selective formation of 6-aryl/alkyl benzo[a]carbazoles, 5-acylbenzo[a]carbazoles, 6-amino-5-acylbenzo[a]carbazoles or 12-methylindolo[2,1-a]isoquinolines, respectively. Mechanistically, the formation of the title compounds involves a cascade process including metalation of the inert C(sp2)?H bond, migratory insertion of ylide into the carbon-metal bond via an in situ carbenoid formation, protodemetalation, and condensation. To our knowledge, this is the first example in which β-carbonyl sulfoxonium ylides were used as stable carbene precursors and bifunctional C2 synthons to afford benzo[a]carbazoles and indolo[2,1-a]isoquinolines. (Figure presented.).
