33555-28-1Relevant academic research and scientific papers
Polysubstituted Indole Synthesis via Palladium/Norbornene Cooperative Catalysis of Oxime Esters
Liu, Jiechun,Lin, Haojiang,Jiang, Huanfeng,Huang, Liangbin
supporting information, p. 484 - 489 (2022/01/20)
Polysubstituted indoles are prevalent in pharmaceuticals, agrochemicals, and organic materials. Presented herein is the fact that polyfunctionalized indoles can be efficiently constructed from easily accessible oxime esters and aryl iodides, involving a palladium/norbornene synergistic synthesis. The reaction is enabled by a unique class of electrophiles in palladium/norbornene cooperative catalysis, which are oxime esters derived from simple ketone. The broad substrate scope and high functional group tolerance could make this method attractive for the synthesis of polysubstituted indoles.
Method for synthesizing 2-substituted indole compound from iodobenzene and oxime ester under catalysis of palladium
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Paragraph 0358-0365, (2022/01/05)
The invention belongs to the technical field of organic chemistry, and discloses a method for synthesizing a 2-substituted indole compound from iodobenzene and oxime ester under the catalysis of palladium. The method comprises the following steps of reacting an oxime ester compound with iodobenzene under the action of a palladium catalyst, a phosphine ligand and norbornene by taking an organic solvent as a reaction medium in a protective atmosphere, and carrying out subsequent treatment to obtain the 2-substituted indole compound. According to the method, palladium is used as a catalyst, the phosphine ligand is adopted, the yield is high, and the substrate applicability is wide. In addition, the oxime ester compound is used as a raw material, and the method has the advantages of cheap and easily-prepared raw materials, simple operation, mild reaction conditions and the like.
Synthesis of Indoles and Pyrroles Utilizing Iridium Carbenes Generated from Sulfoxonium Ylides
Vaitla, Janakiram,Bayer, Annette,Hopmann, Kathrin H.
, p. 4277 - 4281 (2017/04/03)
Metal carbenes can undergo a myriad of synthetic transformations. Sulfur ylides are potential safe precursors of metal carbenes. Herein, we report cascade reactions that involve carbenoids derived from sulfoxonium ylides for the efficient and regioselective synthesis of indoles and pyrroles. The tandem action of iridium and Br?nsted acid catalysts enables rapid assembly of the heterocycles from unmodified anilines or readily accessible enamines under microwave irradiation. The key mechanistic steps are the catalytic transformation of the sulfoxonium ylide into an iridium–carbene complex, followed by N?H or C?H functionalization of an aniline or enamine, respectively, and a final acid-catalyzed cyclization. The present method was successfully applied to the synthesis of the densely functionalized pyrrole subunit of atorvastatin.
Catalytic Synthesis of Substituted Indoles and Quinolines from the Dehydrative C-H Coupling of Arylamines with 1,2- and 1,3-Diols
Lee, Hanbin,Yi, Chae S.
supporting information, p. 1973 - 1977 (2016/07/06)
The cationic ruthenium-hydride complex catalyzes the dehydrative C-H coupling reaction of arylamines with 1,2-diols to form the indole products. The analogous coupling of arylamines with 1,3-diols afforded the substituted quinolines. The catalytic method directly forms these coupling products in a highly regioselective manner without generating any toxic byproducts.
