108501-85-5Relevant articles and documents
Palladium-Catalyzed Synthesis of Dihydrobenzoindolones via C-H Bond Activation and Alkyne Insertion
Rodríguez, José F.,Marchese, Austin D.,Lautens, Mark
, p. 4367 - 4370 (2018)
A palladium-catalyzed intramolecular carbopalladation, intramolecular C-H bond activation, and alkyne insertion sequence for the generation of dihydrobenzoindolones is described. Products are obtained in moderate to excellent yields as single regioisomers
Synthesis and cytotoxic activity of novel hexahydropyrrolo[2,3-b]indole imidazolium salts
Zhou, Yunjing,Duan, Kunyun,Zhu, Liang,Liu, Zhengfeng,Zhang, Chaobo,Yang, Lijuan,Li, Minyan,Zhang, Hongbin,Yang, Xiaodong
, p. 460 - 465 (2016)
A series of novel hexahydropyrrolo[2,3-b]indole-1H-imidazolium salts were synthesized and evaluated in vitro against a panel of human tumor cell lines. The results suggest that the 5,6-dimethyl-benzimidazole ring, and substitution of the imidazolyl-3-posi
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.
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
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
supporting information, 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.
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
Synthesis of oxindoles via Cu-mediated reactions between N-phenylacrylamides and ethyl 2-bromo-2-methylpropionate
Liu, Da,Zhuang, Shaobo,Chen, Xiang,Yu, Lin,Yu, Yongqi,Hu, Liang,Tan, Ze
supporting information, p. 612 - 616 (2018/01/18)
A novel way of synthesizing alkylated oxindoles via Cu-mediated atom transfer radical addition reaction between N-phenylacrylamides and ethyl 2-bromo-2-methylpropionate has been described. It was found that the use of N,N,N′,N′-1,1,2,2,-tetramethylethylenediamine as ligand was important for achieving good yields. Additionally, the use of DMSO as solvent and running the reaction at 130 °C were also crucial. In some cases, the product can be further brominated when the reaction temperature was raised to 150 °C.
