- Copper-mediated rapid and facile oxidative dehydrogenation of dihydrobenzocarbazoles
-
Rapid method for the oxidative dehydrogenation of dihydrobenzocarbazoles has been introduced by using bench scale and commercially available reagent; copper chloride, in excellent yield with easy workup. The scope of the reaction has been studied with broad range of substitutes.
- Humne, Vivek T.,Ulhe, Avinash G.
-
supporting information
(2020/03/16)
-
- Visible-light-induced oxidation/[3 + 2] cycloaddition/oxidative aromatization to construct benzo[ a]carbazoles from 1,2,3,4-tetrahydronaphthalene and arylhydrazine hydrochlorides
-
An efficient synthesis of benzo[a]carbazoles via visible-light-induced tandem oxidation/[3 + 2] cycloaddition/oxidative aromatization reactions was reported. The benzylic C(sp3)-H of tetrahydronaphthalene was activated through visible-light photoredox catalyst with oxygen as the clean oxidant under mild reaction conditions. This protocol proceeds efficiently with broad substrate scope, and the mechanism study was performed.
- Shen, Jiaxuan,Li, Nannan,Yu, Yanjiang,Ma, Chunhua
-
supporting information
p. 7179 - 7183
(2019/09/30)
-
- Relay Catalysis of Bismuth Trichloride and Byproduct Hydrogen Bromide Enables the Synthesis of Carbazole and Benzo[α]carbazoles from Indoles and α-Bromoacetaldehyde Acetals
-
Benzo[α]carbazoles were synthesized from 2-phenylindoles and α-bromoacetaldehyde using bismuth trichloride as a catalyst. The reaction was triggered by a bismuth trichloride-catalyzed Friedel-Crafts alkylation of these two precursors, which provided a tryptaldehyde intermediate that underwent intramolecular olefination to form the final product. Interestingly, the HBr byproduct generated in the upstream step of the reaction catalyzed the following downstream reaction steps, thus creating a byproduct-participated relay catalytic process. Motivated by this mechanism, we developed a three-component reaction of indole, α-bromoacetaldehyde acetal, and 1,3-dicarbonyl compounds. This study offers a straightforward method for synthesizing substituted carbazoles. (Figure presented.).
- Wu, Fengtian,Huang, Wenbo,Yiliqi,Yang, Jian,Gu, Yanlong
-
p. 3318 - 3330
(2018/08/01)
-
- Palladium-catalyzed α-arylation of enones in the synthesis of 2-alkenylindoles and carbazoles
-
A new unified strategy has been developed for the synthesis of substituted 2-alkenylindoles and carbazoles. The strategy uses palladium-catalyzed α-arylation of TES-enol ethers of enones as the key step. The method is highly regioselective, provides good yields, and is expected to have wide application.
- Kale, Ajit Prabhakar,Kumar, Gangam Srikanth,Mangadan, Arun Raj Kizhakkayil,Kapur, Manmohan
-
supporting information
p. 1324 - 1327
(2015/03/14)
-
- Rapid synthesis of fused N-heterocycles by transition-metal-free electrophilic amination of arene C-H bonds
-
We disclose an efficient and operationally simple protocol for the preparation of fused N-heterocycles starting from readily available 2-nitrobiaryls and PhMgBr under mild conditions. More than two dozen N-heterocycles, including two bioactive natural products, have been synthesized using this method. A stepwise electrophilic aromatic cyclization mechanism was proposed by DFT calculations. Controlled fusion: A transition-metal-free, low-temperature, and regioselective intramolecular amination of aromatic C(sp2)-H bonds provides fused N-heterocycles. This reaction is operationally simple and scalable (1-10 mmol) and the scope of substrates is wide (see scheme). Density functional calculations indicate that a stepwise electrophilic aromatic cyclization mechanism may be operative.
- Gao, Hongyin,Xu, Qing-Long,Yousufuddin, Muhammed,Ess, Daniel H.,Kuerti, Laszlo
-
supporting information
p. 2701 - 2705
(2014/03/21)
-