64648-57-3Relevant academic research and scientific papers
Transition-metal-free α-arylation of oxindoles: Vi a visible-light-promoted electron transfer
Liang, Kangjiang,Li, Na,Zhang, Yang,Li, Tao,Xia, Chengfeng
, p. 3049 - 3053 (2019/03/13)
An operationally simple photochemical strategy for the direct arylation of oxindoles with (hetero)aryl halides in the absence of both transition metals and photoredox catalysts has been developed. The reaction provides an efficient way to construct various 3-aryloxindole building blocks of pharmaceutical interest at ambient temperature by using household compact fluorescent light (CFL) bulbs as the light source. Preliminarily, mechanistic studies revealed that the intermolecular electron transfer relied on the formation of photon-absorbing electron-donor-acceptor (EDA) complexes between electron-rich oxindole enolates and electron-deficient (hetero)aryl halides, and a radical chain mechanism was operative.
Enantioselective Arylation of Oxindoles Using Modified BI-DIME Ligands
Mangunuru, Hari P. R.,Malapit, Christian A.,Haddad, Nizar,Reeves, Jonathan T.,Qu, Bo,Rodriguez, Sonia,Lee, Heewon,Yee, Nathan K.,Song, Jinhua J.,Busacca, Carl A.,Senanayake, Chris H.
, p. 4435 - 4443 (2018/11/21)
The Pd-catalyzed 3-arylation of 2-oxindoles with aryl bromides, chlorides and triflates is found to proceed using i -Pr-BI-DIME and Me 2 -BI-DIME ligands. The mono-arylation of 3-unsubstituted oxindoles is accomplished using a Pd 2 (dba) 3 / i -Pr-BI-DIME catalyst system, and gives good yields of 3-aryloxindoles from aryl bromides and chlorides. The arylation of 3-substituted oxindoles is also possible using this catalyst/ligand system. The asymmetric arylation of 3-substituted oxindoles is accomplished using Me 2 -BI-DIME to furnish oxindoles bearing a quaternary C-3 stereocenter in enantiomeric ratios of up to 93:7.
DMF-Promoted Redox-Neutral Ni-Catalyzed Intramolecular Hydroarylation of Alkene with Simple Arene
Lu, Ke,Han, Xing-Wang,Yao, Wei-Wei,Luan, Yu-Xin,Wang, Yin-Xia,Chen, Hao,Xu, Xue-Tao,Zhang, Kun,Ye, Mengchun
, p. 3913 - 3917 (2018/05/22)
A redox-neutral Ni-catalyzed intramolecular hydroarylation of alkene with simple arene has been developed, in which DMF played a proton shuttle role in facilitating the intramolecular coupling, avoiding the use of additional reductants and oxidants. A series of oxindoles with a quaternary center were obtained in up to 99% yield.
Oxindole synthesis by direct coupling of Csp2-H and C sp3-H centers
Jia, Yi-Xia,Kuendig, E. Peter
supporting information; experimental part, p. 1636 - 1639 (2009/06/30)
(Chemical Equation Presented) An sp2/sp3 get-together: A novel and efficient method can be used to synthesize 3,3-disubstitued oxindoles by the direct intramolecular oxidative coupling of an aryl Csp2-H and a Csp3-H center (see scheme; DMF = N,N-dimethylformamide).
