54879-94-6Relevant academic research and scientific papers
Nickel-catalyzed decarbonylative and decarboxylative cycloaddition of isatoic anhydrides with alkynes
Nakai, Kenichiro,Kurahashi, Takuya,Matsubara, Seijiro
, p. 1238 - 1240 (2013)
We have developed a nickel-catalyzed cycloaddition of isatoic anhydrides with alkynes to afford 2,3-disubstituted indoles. The reaction proceeds via the elimination of carbon monoxide and carbon dioxide and the insertion of alkynes.
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.
Assembly of Indole Cores through a Palladium-Catalyzed Metathesis of Ar-X σ-Bonds
Ferrier, Robert C.,Ghasemi, Mehran,Habibi, Azizollah,Jafarpour, Farnaz,Navid, Hamed,Rajai-Daryasarei, Saideh,Safaie, Niloofar
supporting information, p. 9556 - 9561 (2020/12/21)
We describe the development of a new method for construction of highly substituted indole scaffolds through the strategic utilizing of the metathesis of Ar-X σ-bonds based on the dynamic nature of palladium-based oxidative addition/reductive elimination. A suitable and simple catalytic system has provided an appropriate platform for a productive ligand exchange and consecutive carbopalladation/C-H activation/amination of phosphine ligands with alkynes and aromatic/aliphatic amines for construction of structurally diverse indoles.
Indole derivative and its preparation method (by machine translation)
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Paragraph 0047-0051; 0085-0089, (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)
A Fast Track to Indoles and Annulated Indoles through ortho- vs ipso-Amination of Aryl Halides
Jafarpour, Farnaz,Ghasemi, Mehran,Mohaghegh, Farid,Asgari, Sara,Habibi, Azizollah
supporting information, p. 10143 - 10148 (2019/12/24)
A complementary site selective ortho- vs ipso-amination of aryl halides using non-electrophilic amine sources for construction of indole scaffolds is reported. A palladium-catalyzed alkyne insertion/C-H activation/palladacycle amination via merger of three easily diversified components including iodoarenes, alkynes, and amines delivers indoles with different substitution patterns even in gram scales. By employing ortho-bromoanilines, a consecutive annulative π-extension of indoles proceeds to construct indolo[1,2-f]phenanthridine scaffolds via four C-C and C-N bond formations in one pot.
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.
Co(III)-Catalyzed, Internal and Terminal Alkyne-Compatible Synthesis of Indoles
Zhou, Shuguang,Wang, Jinhu,Wang, Lili,Chen, Kehao,Song, Chao,Zhu, Jin
supporting information, p. 3806 - 3809 (2016/08/16)
A Co(III)-catalyzed, internal and terminal alkyne-compatible indole synthesis protocol is reported herein. The N-amino (hydrazine) group imparts distinct, diverse reactivity patterns for directed C-H functionalization/cyclization reactions. Notable synthetic features include regioselectivity for a meta-substituted arylhydrazine, regioselectivity for a chain-branched terminal alkyne, formal incorporation of an acetylenic unit through C2-desilylation on a C2-silylated indole derivative, formal inversion of regioselectivity through consecutive C3-derivatization and C2-desilylation processes, and formal bond migration for a linear-chain terminal alkyne.
Selective Synthesis of N-Unsubstituted and N-Arylindoles by the Reaction of Arynes with Azirines
Thangaraj, Manikandan,Bhojgude, Sachin Suresh,Jain, Shailja,Gonnade, Rajesh G.,Biju, Akkattu T.
, p. 8604 - 8611 (2016/09/28)
The transition-metal-free and temperature-dependent highly selective reaction of arynes with 2H-azirines allowing the synthesis of either N-unsubstituted or N-arylindoles has been developed. At 60 °C, arynes generated from 2-(trimethylsilyl)aryl triflates smoothly insert into 2H-azirines to form 2,3-diarylindoles with high selectivity. Interestingly, when the reaction was performed at -10 °C, the selectivity was switched to the formation of 1,2,3-triarylindoles in good yields.
Cationic Cobalt(III) Catalyzed Indole Synthesis: The Regioselective Intermolecular Cyclization of N-Nitrosoanilines and Alkynes
Liang, Yujie,Jiao, Ning
supporting information, p. 4035 - 4039 (2016/03/19)
The unique regioselectivity and reactivity of cobalt(III) in the direct cyclization of N-nitrosoanilines with alkynes for the expedient synthesis of N-substituted indoles is demonstrated. In the presence of a cobalt(III) catalyst, high regioselectivity was observed when using unsymmetrical meta-substituted N-nitrosoanilines. Moreover, internal alkynes bearing electron-deficient groups, which are almost unreactive in the [Cp?RhIII]-catalyzed system, display good reactivity in this transformation.
Transition-metal-free synthesis of multisubstituted N-arylindoles via reaction of arynes and α-amino ketones
He, Lin,Pian, Ji-Xin,Shi, Jun-Feng,Du, Guang-Fen,Dai, Bin
, p. 2400 - 2405 (2014/04/03)
A simple transition-metal-free protocol for the synthesis of indoles has been developed using aryne cycloaddition. The in situ-generated arynes couple with α-amino ketones through a one-step N-arylation-nucleophilic addition process under mild conditions and efficiently produce multisubstituted N-arylindoles.
