24075-47-6Relevant academic research and scientific papers
Redox-neutral decarboxylative photocyclization of anthranilic acids
Huang, Huawen,Deng, Kun,Deng, Guo-Jun
, p. 8243 - 8247 (2020/12/29)
A mild metal-, catalyst-, and oxidant-free photoredox neutral system has been found to efficiently enable intramolecular decarboxylative cyclization of anthranilic acids. This facile protocol provides an alternative method for the synthesis of carbazoles. Mechanistic studies reveal a key photoinduced 6π-electrocyclization process and formic acid was released as the sole byproduct.
Pd-Catalyzed Intramolecular Chemoselective C(sp2)-H and C(sp3)-H Activation of N-Alkyl- N-arylanthranilic Acids
Hu, Zhe-Yao,Zhang, Yan,Li, Xin-Chang,Zi, Jing,Guo, Xun-Xiang
supporting information, p. 989 - 992 (2019/05/16)
A controllable palladium-catalyzed intramolecular C-H activation of N-alkyl-N-arylanthranilic acids has been developed. The methodology allows selective synthesis of 1,2-dihydro-(4H)-3,1-benzoxazin-4-ones and carbazoles from the same starting materials and palladium catalyst. The selectivity is controlled by the oxidant. Silver oxide promotes C(sp3)-H activation/C-O cyclization to provide 1,2-dihydro-(4H)-3,1-benzoxazin-4-ones, while copper acetate contributes to C(sp2)-H activation/decarboxylative arylation to afford carbazoles. This protocol is demonstrated by its wide substrate scope and good functional group tolerance.
Method for preparing carbazole compound
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Paragraph 0068; 0069; 0070; 0071; 0072; 0073, (2019/04/13)
The invention discloses a method for synthesizing a carbazole compound by utilizing N,N-di-substituted o-aminobenzoate compound. The synthesis method comprises the following steps of adopting a palladium salt as a catalyst, mixing the palladium salt, the N,N-di-substituted o-aminobenzoate compound, an oxidant and an organic solvent, and carrying out heating reaction to obtain the carbazole compound. The method disclosed by the invention has the advantages that the preparation route is short, the universality of a substrate is good, the synthesis yield is high, the used catalyst is simple and easy to obtain and the like.
Photoinduced Cross-Coupling of Amines with 1,2-Diiodobenzene and Its Application in the Synthesis of Carbazoles
Zhao, Xinxin,Chen, Ming,Huang, Binbin,Yang, Chao,Gao, Yuan,Xia, Wujiong
, p. 2981 - 2989 (2018/05/15)
A facile and efficient process for the preparation of various tertiary aminobenzenes and carbazole derivatives via photoinduced cross-coupling of amines with 1,2-diiodobenzene is reported. Mechanistic investigations indicate that the transformation proceeds via nucleo-philic addition of an amine to the benzyne intermediate accompanied with a proton transfer process, followed by an oxidative cyclization of the generated diphenylamine to furnish the corresponding carbazole products.
An Expedient Synthesis of Carbazoles through Potassium tert-Butoxide-Promoted Intramolecular Direct C–H Bond Arylation
Lin, Songbo,He, Xingrui,Meng, Jinpeng,Gu, Haining,Zhang, Peizhi,Wu, Jun
supporting information, p. 443 - 447 (2017/02/05)
Transition-metal-free access to carbazoles was achieved through base-mediated intramolecular C–C bond formation. Reactions of N-substituted o-halodiarylamines with potassium tert-butoxide in the presence of ethylene glycol or 1,10-phenanthroline provided carbazoles in moderate to excellent yields. This transformation may proceed through a radical pathway according to a control experiment with a radical scavenger.
Palladium Nanoparticles in Water: A Reusable Catalytic System for the Cycloetherification or Benzannulation of α-Allenols
Alcaide, Benito,Almendros, Pedro,González, Ana M.,Luna, Amparo,Martínez-Ramírez, Sagrario
, p. 2000 - 2006 (2016/07/06)
A convenient ligand-free catalytic system has been developed for the chemoselective cyclization reaction of various α-allenol derivatives by palladium nanoparticles (PdNPs) in an aqueous reaction medium. (Figure presented.) .
Nickel-catalyzed cross-coupling of anisole derivatives with trimethylaluminum through the cleavage of carbonoxygen bonds
Morioka, Toshifumi,Nishizawa, Akihiro,Nakamura, Keisuke,Tobisu, Mamoru,Chatani, Naoto
supporting information, p. 1729 - 1731 (2016/02/19)
Nickel-catalyzed cross-coupling of methoxyarenes with trimethylaluminum is described. The use of 1,3-dicyclohexylimidazol-2-ylidene as a ligand and NaO'Bu as a base promotes the methylation of anisole derivatives via the cleavage of normally unreactive aryl carbonoxygen bonds.
Iodine recycling via 1,3-migration in iodoindoles under metal catalysis
Alcaide, Benito,Almendros, Pedro,Alonso, Jose M.,Cembellin, Sara,Fernandez, Israel,Del Campo, Teresa Martinez,Torres, M. Rosario
supporting information, p. 7779 - 7781 (2013/09/02)
3-Substituted (indol-2-yl)-α-allenols show divergent patterns of reactivity under metal catalysis. An unprecedented intramolecular 1,3-iodine migration is described.
Palladium-catalyzed carbocyclization-cross-coupling reactions of two different allenic moieties: Synthesis of 3-(buta-1,3-dienyl) carbazoles and mechanistic insights
Alcaide, Benito,Almendros, Pedro,Alonso, Jose M.,Fernandez, Israel
supporting information; experimental part, p. 6604 - 6606 (2012/08/08)
A palladium-catalyzed chemo-, regio- and stereoselective carbocyclization-cross-coupling sequence of two different α-allenols to afford 3-(E-buta-1,3-dienyl) carbazoles is reported.
Gold- or palladium-catalyzed allene carbocyclization/functionalization: Simple and efficient synthesis of carbazoles
Alcaide, Benito,Almendros, Pedro,Alonso, Jose M.,Quiros, M. Teresa,Gadzinski, Pawel
supporting information; experimental part, p. 1871 - 1876 (2011/10/04)
Gold- and palladium-catalyzed cyclization of easily accessible indole-tethered allenols allows the efficient synthesis of carbazole derivatives under mild conditions. Copyright
