2169-37-1Relevant academic research and scientific papers
Electrochemical Palladium-Catalyzed Intramolecular C—H Amination of 2-Amidobiaryls for Synthesis of Carbazoles
Gao, Xinlong,Lei, Aiwen,Wang, Pan,Wang, Qingqing,Zhang, Heng,Zhang, Xiaojing
supporting information, p. 143 - 148 (2020/12/18)
The synthesis of carbazoles based on the electrochemical Pd-catalyzed intramolecular C—H amination of 2-amidobiaryls through oxidative cross coupling has been achieved under mild reaction conditions. The reaction can be carried out in undivided cell without the addition of external chemical oxidant. Besides good functional group compatibility, the desired carbazoles can be scaled up and modified easily. Compared with previous methods, this protocol affords a simple and sustainable avenue for the construction of carbazoles.
Preparation method of carbazole compound
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Paragraph 0043-0051, (2020/08/17)
The invention relates to a preparation method of a carbazole compound. The method comprises the following steps: adding a reaction substrate as shown in a formula (III) into a solvent for dissolving,adding cyclic diacyl peroxide and transition metal, and
Silver-copper co-catalyzed cascade intramolecular cyclization/desulfinamide/dehydrogenation: One-pot synthesis of substituted carbazoles
Huang, Yuanqiong,Guo, Zhonglin,Song, Hongjian,Liu, Yuxiu,Wang, Qingmin
, p. 7143 - 7146 (2018/07/05)
Herein, a silver and copper co-catalyzed cascade intramolecular cyclization/desulfinamide/dehydrogenation reaction for the synthesis of substituted carbazoles is reported. This reaction, which involved formation of new C-C and C-N bonds as well as C-N bond cleavage, afforded diverse carbazoles in high yields and showed good functional group tolerance.
The carbazole compound manufactured by the manufacturing method in the carbazole compound.
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Paragraph 0037-0040; 0042-0057, (2020/10/19)
PROBLEM TO BE SOLVED: To provide a more simple method of manufacturing carbazoles which can be used industrially.SOLUTION: There is provided a manufacturing method of carbazoles including reacting 2-aminobiphenyls of which an amino group is represented by the formula (1), -NHR(1), where Rrepresents S(=O)R, C(=O)Ror an alkyl group having 1 to 3 carbon atoms, where Rrepresents a phenyl group may be substituted by an alkyl group having 1 to 2 carbon atoms or a nitro group, or an alkyl group having 1 to 3 carbon atoms, Rrepresents an alkyl group having 1 to 5 carbon atoms, with a sulfur-based solvent and oxygen in a presence of a heterogeneous catalyst carrying palladium, for example [P9-Type][UL-Type][P60-Type] provided by N.E. CHEMCAT CORPORATION and the like, at 110 to 130°C.
Reductive C(sp2)-N elimination from isolated Pd(IV) amido aryl complexes prepared using H2O2 as oxidant
Abada, Elikplim,Zavalij, Peter Y.,Vedernikov, Andrei N.
supporting information, p. 643 - 646 (2017/05/16)
Di-2-pyridyl ketone (dpk)-supported amidoarylpallada(Il)cycles derived from various 2-(N-R-amino)biphenyls (R = H, Me, CF3CO, MeSOj, CF3SO2) react with hydrogen peroxide in MeOH, THF, MeCN or AcOH to form the corresponding C-N coupled products, N-R-substituted carbazoles, in 82-98% yield. For R = MeS02 and CF3SO2, the corresponding reaction intermediates, amidoaryl Pd(IV) complexes were isolated and characterized by single crystal X-ray diffraction and/or NMR spectroscopy. For the first time, the C(sp2)-N reductive elimination from isolated amidoaryl Pd(lV) complexes has been studied in detail.
Transition-metal-free and organic solvent-free conversion of N-substituted 2-aminobiaryls into corresponding carbazoles via intramolecular oxidative radical cyclization induced by peroxodisulfate
Natarajan, Palani,Priya,Chuskit, Deachen
, p. 5854 - 5861 (2017/12/26)
An atom-economical and environmentally benign approach for the synthesis of N-substituted carbazoles from analogous 2-aminobiaryls using peroxodisulfate in water is reported. The reactions proceeded through an intramolecular oxidative radical cyclization
Palladium on Carbon-Catalyzed C?H Amination for Synthesis of Carbazoles and its Mechanistic Study
Monguchi, Yasunari,Okami, Hiroki,Ichikawa, Tomohiro,Nozaki, Kei,Maejima, Toshihide,Oumi, Yasunori,Sawama, Yoshinari,Sajiki, Hironao
, p. 3145 - 3151 (2016/10/09)
10% Palladium on carbon (10% Pd/C) successfully catalyzed the intramolecular C?H amination of various N-mesylated 2-aminobiphenyls in the presence of a catalytic amount of pyridine N-oxide in heated dimethyl sulfoxide (DMSO) under an oxygen atmosphere to afford the corresponding N-mesylcarbazoles. The reaction would proceed via a single-electron transfer process based on its significant suppression by the addition of a single-electron scavenger, tetracyanoquinodimethane (TCNQ), and the substituents on the aromatic rings of the substrate have an insignificant effect on the reaction progress. (Figure presented.).
Synthesis of Carbazoles by a Merged Visible Light Photoredox and Palladium-Catalyzed Process
Choi, Sungkyu,Chatterjee, Tanmay,Choi, Won Joon,You, Youngmin,Cho, Eun Jin
, p. 4796 - 4802 (2015/08/18)
Carbazoles have attracted great interest in recent years for a variety of applications in organic and medicinal chemistry as well as in materials science. In this work, an efficient method for the synthesis of carbazoles through the intramolecular C-H bon
Pd-catalyzed intramolecular oxidative C-H amination: Synthesis of carbazoles
Youn, So Won,Bihn, Joon Hyung,Kim, Byung Seok
supporting information; experimental part, p. 3738 - 3741 (2011/09/13)
A Pd-catalyzed oxidative C-H amination of N-Ts-2-arylanilines under ambient temperature using Oxone as an inexpensive, safe, and easy-to-handle oxidant has been developed. This process represents a green and practical method for the facile construction of carbazoles with a broad substrate scope and wide functional group tolerance.
Synthesis of carbazoles and dibenzofurans via cross-coupling of o-iodoanilines and o-iodophenols with silylaryl triflates and subsequent Pd-catalyzed cyclization
Liu, Zhijian,Larock, Richard C.
, p. 347 - 355 (2007/10/03)
An efficient route to a variety of carbazoles and dibenzofurans has been developed. It involves the reaction of o-iodoanilines or o-iodophenols with silylaryl triflates in the presence of CsF to afford the N- or O-arylated products, which are subsequently cyclized using a Pd catalyst to carbazoles and dibenzofurans in good to excellent yields. By using this methodology, the carbazole alkaloid, mukonine has been synthesized in 76% overall yield in three steps.
