- Ligand-free iron-catalyzed benzylic C (sp3)-H amination of methylarenes with: N -fluorobenzenesulfonimide
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Direct conversion of cheap methylarenes to benzylic amines, which are essential structural units of important drugs, is of great significance. However, the known methodologies suffer from the requirement of noble metal catalysts, heavy metal residues or s
- Bao, Fengyu,Cao, Yuanbo,Liu, Wenbo,Zhu, Junhao
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p. 27892 - 27895
(2019/09/30)
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- Late-Stage Functionalization of Arylacetic Acids by Photoredox-Catalyzed Decarboxylative Carbon–Heteroatom Bond Formation
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The rapid transformation of pharmaceuticals and agrochemicals enables access to unexplored chemical space and thus has accelerated the discovery of novel bioactive molecules. Because arylacetic acids are regarded as key structures in bioactive compounds, new transformations of these structures could contribute to drug/agrochemical discovery and chemical biology. This work reports carbon–nitrogen and carbon–oxygen bond formation through the photoredox-catalyzed decarboxylation of arylacetic acids. The reaction shows good functional group compatibility without pre-activation of the nitrogen- or oxygen-based coupling partners. Under similar reaction conditions, carbon–chlorine bond formation was also feasible. This efficient derivatization of arylacetic acids makes it possible to synthesize pharmaceutical analogues and bioconjugates of pharmaceuticals and natural products.
- Sakakibara, Yota,Ito, Eri,Fukushima, Tomohiro,Murakami, Kei,Itami, Kenichiro
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supporting information
p. 9254 - 9258
(2018/06/04)
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- N-alkyl/alkenyl sulfimide derivative as well as preparation method and application thereof
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The embodiment of the invention discloses an N-alkyl/alkenyl sulfimide derivative and belongs to the technical field of organic synthesis. The N-alkyl/alkenyl sulfimide derivative has a structure shown in a general formula (I), wherein R is selected from alkyl or alkenyl of which the carbon atom number is 1-6; the alkyl and the alkenyl are independently replaced with phenyl, substituted phenyl, S atom-containing five-membered heterocycle and naphthyl separately. The N-alkyl/alkenyl sulfimide derivative is obtained through intermolecular decarboxylation coupling reaction on a carboxylic acid compound and N-fluoro-diphenylsulfonylamine as raw materials and 1,10-phenanthroline as a ligand in a non-aqueous solvent under the action of a catalyst; the high-purity N-alkyl/alkenyl sulfimide derivative can be efficiently and monoselectively prepared. A biological activity test result shows that the compound synthesized by the N-alkyl/alkenyl sulfimide derivative has a good insecticidal effect and can be widely applied to multiple fields, such as zoology, botany and medicine. The general formula is as shown in the specification.
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Paragraph 0030; 0031; 0032; 0033; 0034; 0035; 0036; 0037
(2018/02/04)
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- Copper(i)-catalyzed radical decarboxylative imidation of carboxylic acids with N-fluoroarylsulfonimides
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An efficient copper-catalyzed radical decarboxylative imidation reaction is presented. This strategy is carried out through the copper(i)-catalyzed decarboxylative C(sp3)-N and C(sp2)-N coupling of carboxylic acids with N-fluoroarylsulfonimides. The reaction shows good functional group tolerance and it provides a new approach for decarboxylative imidation. Preliminary mechanistic studies of this transformation suggest an involvement of N-centered radical species.
- Fang, Zhongxue,Feng, Yu,Dong, Hai,Li, Dashan,Tang, Tiandi
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supporting information
p. 11120 - 11123
(2016/09/19)
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- Highly regioselective copper-catalyzed benzylic C-H amination by N-fluorobenzenesulfonimide
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Primary target: A practical and effective copper-catalyzed amination strategy for synthesizing various benzylic amines from benzylic hydrocarbons is described (see scheme; DCE=1,2-dichloroethane). Xylene substrates can undergo diamination reactions using this method. The remarkable preference for primary over secondary benzylic C-H bonds has been observed for the first time. Copyright
- Ni, Zhikun,Zhang, Qian,Xiong, Tao,Zheng, Yiying,Li, Yan,Zhang, Hongwei,Zhang, Jingping,Liu, Qun
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supporting information; experimental part
p. 1244 - 1247
(2012/03/09)
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- Intermolecular oxidative C-N bond formation under metal-free conditions: Control of chemoselectivity between aryl sp2 and benzylic sp 3 C-H bond imidation
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A new synthetic approach toward intermolecular oxidative C-N bond formation of arenes has been developed under transition-metal-free conditions. Complete control of chemoselectivity between aryl sp2 and benzylic sp 3 C-H bond imidation was achieved by the choice of nitrogen sources, representatively being phthalimide and dibenzenesulfonimide, respectively.
- Kim, Hyun Jin,Kim, Jiyu,Cho, Seung Hwan,Chang, Sukbok
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supporting information; experimental part
p. 16382 - 16385
(2011/12/13)
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