6121-45-5Relevant academic research and scientific papers
An Oxidant- And Catalyst-Free Synthesis of Dibenzo[ a, c ]carbazoles via UV Light Irradiation of 2,3-Diphenyl-1 H -indoles
Hou, Rong,Kang, Yang,Liang, Yong,Min, Xiaoyan,Wang, Tao,Zhang, Zunting
, (2021/12/13)
An efficient methodology for the synthesis of dibenzo[a,c]- carbazoles via annulation of 2,3-diphenyl-1H-indoles in EtOH under UV light irradiation (λO = 365 nm) along with hydrogen evolution is described. This method exhibits the advantages of mild reaction conditions, no requirement of any oxidants and catalysts, and release of hydrogen as the only byproduct. Notably, the mechanism investigation confirms that the trans-4b,8a-dihydro-9H-dibenzo[a,c]carbazole intermediate could convert into cis-4b,8a-dihydro-9H-dibenzo[a,c]carbazole, which relies on the nitrogen atom of the indole ring. This is followed by intramolecular dehydrogenation which yields the dibenzo[a,c]carbazoles. 2021. Thieme. All rights reserved.
Au-promoted Pd-catalyzed arylative cyclization of N,N-dimethyl-o-alkynylaniline with aryl iodides: Access to 2,3-diaryl indoles and mechanistic insight
Yuan, Kemeng,Wang, Jiwei,Wang, Feijun,Zhang, Jun
supporting information, (2021/02/01)
We have developed a Au-promoted Pd-catalyzed cyclization/cross-coupling of N,N-dimethyl-o-alkynylaniline with aryl iododes to synthesize 2,3-diarylindoles under mild and base-free conditions. A related vinyl-Au species has been isolated through Au-promoted cyclization of N,N-dimethyl-o-alkynylaniline and structurally characterized. Further study on its reactivity suggests the vinyl-Au species might be out of catalytic cycle, and PhPd(OTf)(PPh3)2 is probably the reaction intermediate.
Catalytic Arylative Endo Cyclization of Gold Acetylides: Access to 3,4-Diphenyl Isoquinoline, 2,3-Diphenyl Indole, and Mesoionic Normal NHC–Gold Complex
Wang, Jiwei,Yuan, Kemeng,Wang, Gendi,Liu, Ye,Zhang, Jun
, p. 212 - 217 (2020/12/07)
3,4-Diphenyl isoquinoline and 2,3-diphenyl indole are readily accessed by catalytic selective bis-arylative endo cyclization of gold acetylides. The synthetic approach could be also extended to prepare six-membered mesoionic NHC complex, which could furth
One-Pot Tandem ortho-Naphthoquinone-Catalyzed Aerobic Nitrosation of N-Alkylanilines and Rh(III)-Catalyzed C-H Functionalization Sequence to Indole and Aniline Derivatives
Si, Tengda,Kim, Hun Young,Oh, Kyungsoo
, p. 1152 - 1163 (2021/01/14)
The nitroso group served as a traceless directing group for the C-H functionalization of N-alkylanilines, ultimately removed after functioning either as an internal oxidant or under subsequent reducing conditions. The unique ability of o-NQ catalysts to aerobically oxidize the N-alkylanilines without using solvents and stoichiometric amounts of oxidants has rendered the new opportunity to develop the telescoped catalyst systems without a need for directly handling the hazardous N-nitroso compounds.
Room-temperature Pd/Ag direct arylation enabled by a radical pathway
Luscombe, Christine K.,Mayhugh, Amy L.
supporting information, p. 384 - 390 (2020/03/27)
Direct arylation is an appealing method for preparing π-conjugated materials, avoiding the prefunctionalization required for traditional cross-coupling methods. A major effort in organic electronic materials development is improving the environmental and economic impact of production; direct arylation polymerization (DArP) is an effective method to achieve these goals. Room-temperature polymerization would further improve the cost and energy efficiencies required to prepare these materials. Reported herein is new mechanistic work studying the underlying mechanism of room temperature direct arylation between iodobenzene and indole. Results indicate that room-temperature, Pd/Ag-catalyzed direct arylation systems are radical-mediated. This is in contrast to the commonly proposed two-electron mechanisms for direct arylation and appears to extend to other substrates such as benzo[b]thiophene and pentafluorobenzene.
Divergent C-H activation synthesis of chalcones, quinolones and indoles
Shi, Yuesen,Xing, Huimin,Huang, Tianle,Liu, Xuexin,Chen, Jian,Guo, Xiaoyu,Li, Guo-Bo,Wu, Yong
supporting information, p. 1585 - 1588 (2020/02/13)
We here report a condition-controlled divergent synthesis strategy of chalcones, quinolones and indoles, which was achieved via a C-H activation reaction of N-nitrosoanilines and cyclopropenones. Variations of Ag salts are observed to be crucial for divergently constructing the three distinct chemical scaffolds. A Rh(i)- and Rh(iii)-cocatalyzed decarbonylation/C-H activation/[3+2] annulation cascade reaction was developed for the synthesis of indoles. These methodologies are characterized by mild reaction conditions, high functional group tolerance, and amenability to gram-scale synthesis, providing a reference for future derivation of new chemical scaffolds by C-H activation.
Indole derivative and its preparation method (by machine translation)
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Paragraph 0047-0051; 0072-0076, (2019/10/04)
The present invention provides indole derivative and its preparation method, comprises the following steps: a compound represented by formula I, additive and solvent mixed, in nitrogen or argon and visible light illumination under the conditions of reaction, to obtain the indole derivatives. In a nitrogen or argon atmosphere, through visible light radiation excitation I shown in the polyurea compound of carbon oxygen key, then the occurrence of [1, 6] - H migration, eventually through the intramolecular radical coupling and dehydration reaction for the synthesis of indole derivatives, the whole process needs no photocatalyst participation, the operation is simple, mild condition, high yield, accords with the atom economic and environmental protection, for the industrial preparation of indole derivatives having a high reference value. (by machine translation)
Rhodium(iii)-catalyzed indole synthesis at room temperature using the transient oxidizing directing group strategy
Shang, Yaping,Jonnada, Krishna,Yedage, Subhash Laxman,Tu, Hua,Zhang, Xiaofeng,Lou, Xin,Huang, Shijun,Su, Weiping
, p. 9547 - 9550 (2019/08/15)
Rh-catalyzed reactions of N-alkyl anilines with internal alkynes at room temperature have been developed using an in situ generated N-nitroso group as a transient oxidizing directing group. Due to mild reaction conditions, this method enabled synthesis of a broad range of N-alkyl indoles, including even two indole-based medicinal compounds. Our work disclosed the feasibility of the transient oxidizing directing group strategy in C-H functionalization reactions, which possesses the potential to enhance overall step-economy and impart new reactivity patterns to substrates.
Redox-Neutral [4 + 2] Annulation of N-Methoxybenzamides with Alkynes Enabled by an Osmium(II)/HOAc Catalytic System
Yang, Jian,Wu, Liexin,Xu, Huiying,Gao, Hui,Zhou, Zhi,Yi, Wei
supporting information, p. 9904 - 9908 (2019/12/24)
By making use of a direct C-H activation strategy, an efficient osmium(II)-catalyzed redox-neutral [4 + 2] annulation of N-methoxybenzamides with alkynes has been accomplished. Computational and experimental studies revealed that such transformation leading to the synthesis of the isoquinolone core might follow an Os(II)-Os(IV)-Os(II) catalytic pathway, in which an unusual HOAc-assisted oxidative addition of osmium(II) into the N-O bond to generate the osmium(IV) species was involved as one of the key transition states. Further exploration of divergent C-H activation reaction modes enabled by the osmium(II) catalyst has also been exemplified for one-pot assembly of other either linear or cyclic products.
Palladium-Catalyzed Synthesis of 2,3-Diaryl- N-methylindoles from ortho-Alkynylanilines and Aryl Pinacol Boronic Esters
Luo, Yue-Gui,Basha, R. Sidick,Reddy, Daggula Mallikarjuna,Xue, Yong-Jing,Chen, Te-Hsuan,Lee, Chin-Fa
supporting information, p. 6872 - 6876 (2018/11/21)
A palladium-catalyzed synthesis of 2,3-diaryl-N-methylindoles from o-alkynylanilines and aryl pinacol boronic esters was developed. The system possesses high functional group tolerance and a broad substrate scope with a variety of aryl pinacol boronic est
