1449116-83-9Relevant academic research and scientific papers
Synthesis of Dichlorocyanomethyl-Functionalized Oxindoles by Cascade Reactions Initiated by Copper(I)-Catalytically Generated Dichlorocyanomethyl Radical
Che, Fengrui,Hou, Zhichen,Ma, Chaopeng,Wang, Maorong,Yu, Chunzheng,Yu, Linhan,Zhang, Yuexia,Zhong, Jiangbin
, p. 5020 - 5025 (2020)
An efficient and convenient protocol for synthesis of dichlorocyanomethyl-functionalized oxindoles through the cascade reactions of dichlorocyanomethyl radical with N-arylacrylamides is reported. The electrophilic dichlorocyanomethyl radical, which is gen
Silver(I)-mediated oxidation/cyclization of acrylamides with alkyl trifluoroborates
Ding, Siyi,Ren, Huaping,Zhu, Min,Ma, Qiang,Miao, Zongcheng,Li, Pengfei
supporting information, p. 593 - 600 (2020/11/19)
A mild silver-mediated oxidative cyclization of acrylamides has been developed by using alkyl trifluoroborates as radical precursors. It proceeds through a tandem radical addition/cyclization process, in which two new carbon-carbon bonds were formed. This
Copper-Catalyzed Radical N-Demethylation of Amides Using N-Fluorobenzenesulfonimide as an Oxidant
Yi, Xuewen,Yi, Xuewen,Lei, Siyu,Liu, Wangsheng,Che, Fengrui,Yu, Chunzheng,Liu, Xuesong,Wang, Zonghua,Zhou, Xin,Zhang, Yuexia
supporting information, p. 4583 - 4587 (2020/05/05)
An unprecedented N-demethylation of N-methyl amides has been developed by use of N-fluorobenzenesulfonimide as an oxidant with the aid of a copper catalyst. The conversion of amides to carbinolamines involves successive single-electron transfer, hydrogen-atom transfer, and hydrolysis, and is accompanied by formation of N-(phenylsulfonyl)benzenesulfonamide. Carbinolamines spontaneously decompose to N-demethylated amides and formaldehyde, because of their inherent instability.
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
, 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.
A tethering directing group strategy for ruthenium-catalyzed intramolecular alkene hydroarylation
Kilaru, Praveen,Acharya, Sunil P.,Zhao, Pinjing
supporting information, p. 924 - 927 (2018/02/07)
We report a new catalyst design for N-heterocycle synthesis that utilizes an alkene-tethered amide moiety as a directing group for aromatic C-H activation. This tethering directing group strategy is demonstrated in a ruthenium-catalyzed intramolecular alk
Synthesis of oxindoles through silver-catalyzed trifluoromethylation-, difluoromethylation- and arylsulfonylation-cyclization reaction of N-arylacrylamides
Liu, Jidan,Zhuang, Shaobo,Gui, Qingwen,Chen, Xiang,Yang, Zhiyong,Tan, Ze
, p. 3196 - 3202 (2014/06/09)
Efficient synthesis of trifluoromethyl and difluoromethyl-substituted oxindoles was achieved by reacting Langlois reagent or Baran reagent with N-arylacrylamides. However, the reaction of aryl sulfinic acid sodium salts with N-arylacrylamides did not give the desulfinative products, instead, aryl sulfonated products were produced. Copyright
Direct annulations toward phosphorylated oxindoles: Silver-catalyzed carbon-phosphorus functionalization of alkenes
Li, Ya-Min,Sun, Meng,Wang, Hong-Li,Tian, Qiu-Ping,Yang, Shang-Dong
, p. 3972 - 3976 (2013/05/09)
Silver screen: The AgNO3-catalyzed carbon phosphorylation of alkenes occurs by an alkene addition/cyclization cascade. Ag+ reacts with Ph2P(O)H to form the crucial active intermediate 1, which promotes the reaction. This method requires a cheap, nontoxic silver salt as the catalyst and substrates for the transformation are simple and readily accessible.
