- A metal-free synthesis of oxindoles by a radical addition-cyclization onto N-arylacrylamides with xanthates
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A convenient, high yielding synthesis of oxindoles by metal-free di-functionalization of alkenes with xanthates has been developed. This transformation involves a radical addition/cyclization process. Various arylalkylation products including alkyl ester-, benzyl-, cyano-, ketone-, amine-, and amide-substituted oxindoles were prepared in good to excellent yields.
- Wang, Shucheng,Huang, Xuhu,Li, Bowen,Ge, Zemei,Wang, Xin,Li, Runtao
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- Copper-catalyzed alkylarylation of activated alkenes using isocyanides as the alkyl source: An efficient radical access to 3,3-dialkylated oxindoles
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A novel and efficient protocol for the synthesis of 3,3-dialkylated oxindoles is described. The method involves a copper-catalyzed tandem radical addition/cyclization of N-arylacrylamides with the alkyl radicals generated from isocyanides. Two C-C bonds are formed in a single step.
- Zhao, Yaping,Li, Zhenghua,Sharma, Upendra K.,Sharma, Nandini,Song, Gonghua,Van Der Eycken, Erik V.
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- Discovery of an Oxidative System for Radical Generation from Csp3-H Bonds: A Synthesis of Functionalized Oxindoles
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A facile and versatile method for generating radicals from Csp3-H bonds under metal-free and organic-peroxide-free conditions was developed. By combining safe persulfate and low-toxic quaternary ammonium salt, a wide variety of Csp3-H compounds including ethers, (hetero)aromatic/aliphatic ketones, alkylbenzenes, alkylheterocycles, cycloalkanes, and haloalkanes were selectively activated to generate the corresponding C-centered radicals, which could be further captured by N-arylacrylamides to deliver the valuable functionalized oxindoles. Good functional group tolerance was demonstrated. The useful polycarbonyl compound and esters were also modified with the strategy. Moreover, the combination can also be applied to the practical coupling between simple haloalkanes and N-hydroxyphthalimide (NHPI).
- Zhang, Ming-Zhong,Li, Wan-Ting,Li, Yuan-Yuan,Wang, Qi,Li, Chong,Liu, Yan-Hao,Yin, Jin-Xing,Yang, Xin,Huang, Huisheng,Chen, Tieqiao
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p. 15544 - 15557
(2021/10/20)
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- A antibacterial indole preparation method (by machine translation)
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The invention discloses a antibacterial indole preparation method, in particular to to activate the olefin as the substrate of reaction, to palladium metal compound as a catalyst, in order to dppf as a ligand, to undifferentiated as the alkylating agent,
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Paragraph 0053
(2019/02/06)
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- Electrochemical cobalt-catalyzed C-H or N-H oxidation: A facile route to synthesis of substituted oxindoles
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Two comparable protocols for the electrochemical cobalt-catalyzed C-H/N-H oxidation have been exploited for the synthesis of substituted oxindoles via radical pathways. The electrochemical cobalt-catalyzed system was demonstrated to be efficient and eco-friendly and avoided the use of stoichiometric oxidants to afford the arylation or alkylation products in good yields at room temperature.
- Yu, Yue,Zheng, Peifeng,Wu, Yuanheng,Ye, Xiaoyi
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supporting information
p. 8917 - 8921
(2018/12/10)
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- Nickel-Catalyzed Alkylarylation of Activated Alkenes with Benzyl-amines via C?N Bond Activation
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A nickel-catalyzed alkylarylation of active alkenes with tertiary benzylamines was achieved by charge-transfer-complex promoted C?N bond activation. The reaction proceeded through initial Ni-catalyzed C?N bond activation, followed by sequential radical addition, redox and proton abstraction with cleaved amine moiety in the absence of oxidant, and provides an efficient method to prepare various alkyl-substituted oxindoles and dihydroquinolinones in good yields.
- Yu, Hui,Hu, Bin,Huang, Hanmin
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supporting information
p. 7114 - 7117
(2018/05/03)
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- Palladium-catalyzed alkylarylation of acrylamides with unactivated alkyl halides
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An efficient palladium-catalyzed alkylarylation of acrylamides with unactivated alkyl halides has been developed. This method is highlighted by its broad substrate scope and excellent functional group tolerance. In addition to alkyl halides, fluoroalkyl halides and benzyl bromides also participated well in this transformation. A detailed mechanistic investigation suggests that a radical pathway is probably involved in the cyclization process.
- Wang, Hua,Guo, Li-Na,Duan, Xin-Hua
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p. 860 - 867
(2016/02/18)
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- Oxidant-Free Rhodium(I)-Catalyzed Difunctionalization of Acrylamide: An Efficient Approach to Synthesize Oxindoles
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(Figure Presented) The first rhodium(I)-catalyzed difunctionalization of arylacrylamides to synthesize oxindoles is developed, and it does not require the assistance of an oxidant. This method provides an efficient approach to generate various useful functionalized oxindoles, some of which cannot be easily accessed by previous approaches.
- Li, Chen-Chen,Yang, Shang-Dong
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p. 2142 - 2145
(2015/05/13)
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- Free-radical cascade Alkylarylation of Alkenes with simple Alkanes: Highly efficient access to Oxindoles via selective (sp3)C-H and (sp 2)C-H Bond functionalization
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A copper-catalyzed alkylarylation of alkenes with simple alkanes was achieved, which not only provided an efficient method to prepare various alkyl-substituted oxindoles, but also represented a novel strategy for selective sp3 C-H functionalization/C-C bond formation via a free-radical cascade process. Additionally, selective activation of unactivated (sp 3)C-H and (sp2)C-H bonds by one single step is achieved in this system, which would also provide a novel strategy for raising efficiency in C-H bond functionalization.
- Li, Zejiang,Zhang, Ye,Zhang, Lizhi,Liu, Zhong-Quan
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supporting information
p. 382 - 385
(2014/04/03)
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- Oxidative 1,2-difunctionalization of activated alkenes with benzylic C(sp3)-H bonds and aryl C(sp2)-H bonds
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DTBP (di-tert-butyl peroxide) is utilized to mediate oxidative 1,2-difunctionalization of activated alkenes with an aryl C(sp2)-H bond and a benzylic C(sp3)-H bond for the synthesis of functionalized oxindoles. This reaction is a new organomediated strategy for alkene difunctionalization facilitated by Lewis acids. The Royal Society of Chemistry 2013.
- Zhou, Ming-Bo,Wang, Cheng-Yong,Song, Ren-Jie,Liu, Yu,Wei, Wen-Ting,Li, Jin-Heng
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supporting information
p. 10817 - 10819
(2013/11/06)
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- Copper-catalyzed oxidative benzylarylation of acrylamides by benzylic C-H bond functionalization for the synthesis of oxindoles
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Radically changing benzyls: An efficient method for the benzylarylation of activated alkenes has been developed through a copper-catalyzed tandem radical addition/cyclization strategy (see scheme). This oxidative coupling between acrylamides and benzylic hydrocarbons provides access to diverse alkyl-substituted oxindoles in good to excellent yields. A variety of functional groups were tolerated in this transformation (TBPB=tert-butylperoxy benzoate). Copyright
- Zhou, Shi-Liu,Guo, Li-Na,Wang, Hua,Duan, Xin-Hua
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supporting information
p. 12970 - 12973
(2013/10/01)
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