15757-32-1Relevant academic research and scientific papers
Palladium-Catalyzed Allenamide Carbopalladation/Allylation with Active Methine Compounds
Zhu, Xiaoyi,Li, Ruibo,Yao, Hequan,Lin, Aijun
, p. 4630 - 4634 (2021/06/28)
A palladium-catalyzed allenamide carbopalladation/allylation with active methine compounds has been developed. Various indoles and isoquinolinones bearing a quaternary carbon center were achieved with good efficiency, a broad substrate scope and good functional group tolerance. This reaction underwent cascade oxidative addition, carbopalladation, and allylic alkylation, and two new C-C bonds were formed in one pot.
Copper-Catalyzed Asymmetric Propargylic Alkylation with Oxindoles: Diastereo- A nd Enantioselective Construction of Vicinal Tertiary and All-Carbon Quaternary Stereocenters
Xia, Jin-Tao,Hu, Xiang-Ping
supporting information, p. 1102 - 1107 (2020/02/15)
A copper-catalyzed asymmetric propargylic alkylation of propargylic acetates with 3-substituted oxindoles for the stereoselective construction of vicinal tertiary and all-carbon quaternary stereocenters in a 3,3-disubstituted oxindole skeleton has been realized. The reaction proceeded smoothly under the catalysis of Cu(MeCN)4PF6combined with a chiral tridentate ferrocenyl P,N,N ligand, leading to a broad range of optically active 3,3-disubstituted oxindoles in high yields and with excellent diastereo- A nd enantioselectivities.
Visible light mediated aerobic oxidative hydroxylation of 2-oxindole-3-carboxylate esters: An alternative approach to 3-hydroxy-2-oxindoles
Wang, Jinge,Osman, Siyitemer,Lu, Xinjiang,Chen, Junyi,Xia, Xu-Dong
, p. 168 - 175 (2020/12/09)
A convenient aerobic oxidative hydroxylation of 3-substituted oxindoles under mild reaction conditions is described herein. This process was accomplished by the activation of molecular oxygen in the air in the presence of a photocatalyst under the irradiation of visible light. The desired product was delivered in up to 89% yield without the addition of base or stoichiometric oxidant.
Employing Arynes for the Generation of Aryl Anion Equivalents and Subsequent Reaction with Aldehydes
Gaykar, Rahul N.,Bhunia, Anup,Biju, Akkattu T.
, p. 11333 - 11340 (2018/07/21)
Arynes are highly reactive intermediates, which are utilized for the electrophilic arylation of various X-H bonds (X = O, N, S etc.). Herein, a new synthetic strategy is demonstrated, where arynes are converted into aryl anion equivalents by treatment with phosphines and a base. The addition of phosphines to arynes form the phosphonium salts, which in the presence of a carbonate base generates the aryl anion equivalent. Subsequent addition of the aryl anions with aldehydes afforded the secondary alcohols.
Palladium-catalyzed selective synthesis of 3-hydroxy-2-oxindoles via cascade C-H cycloaddition and oxidation of α-Aminoacetophenones
Liao, Yan-Yan,Xu, Li,Tang, Ri-Yuan,Zheng, Wen-Xu
, p. 4645 - 4650 (2019/02/01)
A novel method for the synthesis of 3-hydroxy-2-oxindole (3-hydroxyindolin-2-one) derivatives by palladium-catalyzed tandem C-H cycloaddition and oxidation of α-Aminoacetophenone has been developed. In the presence of Pd(OAc)2 and AgOAc, a variety of 3-hy
Enantioselective Intramolecular Copper-Catalyzed Borylacylation
Whyte, Andrew,Burton, Katherine I.,Zhang, Jingli,Lautens, Mark
, p. 13927 - 13930 (2018/10/02)
An enantioselective copper-catalyzed intramolecular borylacylation is reported. The reaction proceeds through an initial enantioselective borylcupration of the styrene, followed by a nucleophilic attack on the tethered carbamoyl chloride. The products, chiral borylated 3,3-disubstituted oxindoles, were generated in excellent yields and enantioselectivities. The versatile carbon–boron bond provides a platform for a wide array of diversification.
Preparation method of 3-hydroxyl-2-indolone derivative in water phase
-
Paragraph 0081; 0082, (2018/09/11)
The invention relates to a synthesis method of a 3-hydroxyl-2-indolone derivative in a water phase. The method includes the steps: adding 3-replacement-2-indolone compound (1a), a compound as shown ina formula 2a, sodium dodecyl sulfate (SDS) and solvent water into an Schlenk reaction bottle; placing the reaction bottle into a position with atmosphere conditions of a certain temperature and air,and stirring and reacting mixture in the reaction bottle; monitoring reaction processes by a TLC (thin-layer chromatography) or GC (gas chromatography); performing post-processing to obtain a target product 3-hydroxyl-2-indolone derivative (I) until raw materials completely react.
Preparation method of 3-substituted-3-hydroxy-2-indolone compounds
-
Paragraph 0064; 0065; 0066, (2018/03/26)
The invention provides a green synthesis method for preparing 3-substituted-3-hydroxy-2-indolone compounds. In the method, 3-substituted-2-indolone compounds 1a are taken as raw materials, and 3-substituted-3-hydroxy-2-indolone compounds are prepared conveniently with excellent yield under promotion of room temperature and TEMPO and/or other analogue 2a. The preparation method is simple in processand efficient and low in cost.
Co(III)-Catalyzed Coupling-Cyclization of Aryl C-H Bonds with α-Diazoketones Involving Wolff Rearrangement
Hu, Xinwei,Chen, Xun,Shao, Youxiang,Xie, Haisheng,Deng, Yuanfu,Ke, Zhuofeng,Jiang, Huanfeng,Zeng, Wei
, p. 1308 - 1312 (2018/02/14)
An unusual cobalt(III)-catalyzed cross-coupling/cyclization of aryl C-H bonds of N-nitrosoanilines with α-diazo-β-ketoesters has been achieved. This protocol features a unique combination of Csp2-H activation/Wolff rearrangement process, allowing for the rapid assembly of quaternary 2-oxindoles. The empirical evidence and density functional theory (DFT) calculations reveal the trapping process of transient acceptor ketene intermediates by cobalt metallocycles.
Nickel(II)-catalyzed addition reaction of arylboronic acids to isatins
Zhang, Yu-Yang,Chen, Huixuan,Jiang, Xiaoding,Liang, Hao,He, Xuefeng,Zhang, Yaqi,Chen, Xiangmeng,He, Wenhuan,Li, Yongsu,Qiu, Liqin
, p. 2245 - 2250 (2018/04/02)
A Ni-catalyzed addition of arylboronic acids to isatins was first developed. The reaction, driven by Ni(acac)2 and dppp as the phosphine ligand, gave 3-aryl-3-hydroxy-2-oxindoles in up to 97% yield. Scopes of benzyl-protected isatins and arylboronic acids were examined. Substituted phenylboronic acids along with fused-ring and heterocyclic boronic acids reacted with isatins smoothly. Preliminary asymmetric catalysis was investigated as well, showing moderate enantioselectivity. The mechanism was also described.
