1454769-81-3Relevant articles and documents
An approach to spirooxindoles: Via palladium-catalyzed remote C-H activation and dual alkylation with CH2Br2
Shao, Changdong,Wu, Zhuo,Ji, Xiaoming,Zhou, Bo,Zhang, Yanghui
, p. 10429 - 10432 (2017)
A facile and efficient approach for the synthesis of spirooxindoles has been developed via the coupling of spirocyclic C,C-palladacycles with CH2Br2. The key spirocyclic palladacycles are generated catalytically via remote C-H activation. A range of spirooxindoles can be synthesized in good to excellent yields from readily available starting material.
Palladium-Catalyzed Enantioselective Intramolecular Heck Carbonylation Reactions: Asymmetric Synthesis of 2-Oxindole Ynones and Carboxylic Acids
Zhang, Di,Xiong, Youyuan,Guo, Yingjie,Zhang, Lei,Wang, Zheng,Ding, Kuiling
supporting information, (2021/10/25)
Herein, we report a Pd-catalyzed enantioselective domino Heck carbonylation reaction of o-iodoacrylanilides with terminal alkynes and water as the nucleophiles, affording a diversity of β-carbonylated 2-oxindole derivatives bearing a 3,3-disubstituted all-carbon quaternary stereocenter, in high yields (55–99 %) with good to excellent enantioselectivities (up to 99 % ee). The synthetic utilities of the protocol were demonstrated in the gram-scale synthesis of 2-oxindole-derived ynone 3 ea and carboxylic acid 4 a, as well as the facile synthesis of chiral 2-oxindoles with a pyrazole or isoxazole moiety.
Palladium-Catalyzed Domino Heck/Sulfination: Synthesis of Sulfonylated Hetero- And Carbocyclic Scaffolds Using DABCO-Bis(sulfur dioxide)
Bajohr, Jonathan,Diallo, Abdoul G.,Whyte, Andrew,Gaillard, Sylvain,Renaud, Jean-Luc,Lautens, Mark
supporting information, p. 2797 - 2801 (2021/04/13)
The synthesis of a broad variety of hetero- and carbocyclic scaffolds via a Pd-catalyzed domino Heck/SO2 insertion reaction is reported. This reaction utilizes DABSO, a safe and easy-to-handle alternative to SO2 gas. The reaction proceeds through a sulfin
Palladium-Catalyzed Domino Synthesis of 2,3-Difunctionalized Indoles via Migratory Insertion of Isocyanides in Batch and Continuous Flow
Chen, Su,Oliva, Monica,Van Meervelt, Luc,Van der Eycken, Erik V.,Sharma, Upendra K.
supporting information, p. 3220 - 3226 (2021/06/01)
We report, herein, a palladium-catalyzed cascade comprising carbopalladation, migratory insertion of isocyanide and triple bond activation followed by a nucleophilic attack (OR?) to construct difunctionalized acyl indoles. The process involves
Nickel-Catalyzed Arylcarbamoylation of Alkenes of N-(o-Iodoaryl)acrylamides with Nitroarenes via Reductive Aminocarbonylation: Facile Synthesis of Carbamoyl-Substituted Oxindoles
Cheng, Chaozhihui,Xiang, Jian-Nan,Zhu, Yan-Ping,Peng, Zhi-Hong,Li, Jin-Heng
supporting information, p. 9543 - 9547 (2021/12/14)
Nickel-catalyzed arylcarbamoylation reactions of alkenes of N-(o-haloaryl)acrylamides with CO and nitroarenes via reductive aminocarbonylation to produce carbamoyl-substituted oxindoles with an all-carbon quaternary stereogenic center are presented. Starting with N-(o-haloaryl)acrylamides, simple CO, and inexpensive nitroarenes and using a Ni catalyst, a dinitrogen-based ligand, a Zn reductant, a TMSCl additive, and a base system, this protocol enables the synthesis of various carbamoyl-substituted oxindoles and allows the efficient late-stage derivatization of valuable molecules.
3,3′-Disubstituted Oxindoles Formation via Copper-Catalyzed Arylboration and Arylsilylation of Alkenes
Liang, Ren-Xiao,Chen, Ru-Yi,Zhong, Chao,Zhu, Jia-Wen,Cao, Zhong-Yan,Jia, Yi-Xia
, p. 3215 - 3218 (2020/04/10)
Arylboration and arylsilylation reactions of N-(2-iodoaryl)acrylamides with bis(pinacolato)-diboron (B2pin2) or PhMe2Si-Bpin are developed by using simple CuOAc as the sole catalyst. A range of boron-or silane-bearing 3,3′-disubstituted oxindoles are obtained in moderate to excellent yields. The reaction is proposed to proceed via a domino sequence involving intermolecular olefin borylcupration or silylcupration followed by intramolecular coupling of an alkyl-Cu intermediate with aryl iodide.
Pd/Cu-Catalyzed Enantioselective Sequential Heck/Sonogashira Coupling: Asymmetric Synthesis of Oxindoles Containing Trifluoromethylated Quaternary Stereogenic Centers
Bai, Xingfeng,Wu, Caizhi,Ge, Shaozhong,Lu, Yixin
supporting information, p. 2764 - 2768 (2019/12/24)
An asymmetric palladium and copper co-catalyzed Heck/Sonogashira reaction between o-iodoacrylanilides and terminal alkynes to synthesize chiral oxindoles was developed. In particular, a wide range of CF3-substituted o-iodoacrylanilides reacted
Nickel-catalyzed reductive aryl thiocarbonylation of alkene via thioester group transfer strategy
Feng, Yunxia,Yang, Shimin,Zhao, Shen,Zhang, Dao-Peng,Li, Xinjin,Liu, Hui,Dong, Yunhui,Sun, Feng-Gang
supporting information, p. 6734 - 6738 (2020/09/15)
Herein reported is a nickel-catalyzed reductive aryl thiocarbonylation of alkene via thioester group transfer strategy by using simple and readily available thioesters. In contrast to traditional activation of weaker C(acyl)-S bond, the C(acyl)-C bond of
Palladium-Catalyzed Tandem Reaction of Three Aryl Iodides Involving Triple C-H Activation
Luo, Xiai,Xu, Yankun,Xiao, Genhua,Liu, Wenjuan,Qian, Cheng,Deng, Guobo,Song, Jianxin,Liang, Yun,Yang, Chunming
, p. 2997 - 3000 (2018/05/28)
A novel palladium-catalyzed tandem reaction of N-(2-iodoaryl)acrylamides with two aryl iodides for the synthesis of spirooxindole has been achieved. The reaction underwent the process of triple C-H activation and four C-C bond formations based on the double trapping of transient spirocyclic palladacycles which are obtained through remote C-H activation.
Disilylation of N-(2-Halophenyl)-2-phenylacrylamides with hexamethyldisilane via trapping the spirocyclic palladacycles
Xiao, Genhua,Chen, Liang,Deng, Guobo,Liu, Jianbing,Liang, Yun
, p. 1836 - 1840 (2018/04/11)
The palladium-catalyzed disilylation of the spirocyclic palladacycles with hexamethylaisilane has been realized. The key spirocyclic palladacycles are generated from N-(2-haloaryl)-2-arylacrylamide via intramolecular Heck reaction and followed remote C-H activation. A range of 3-((trimethylsilyl)methyl)-3-(2-(trimethylsilyl)phenyl)indolin-2-ones are obtained in good to excellent yields from readily available starting material under mild conditions.
