- Ligand compound for copper catalyzed aryl halide coupling reaction, catalytic system and coupling reaction
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The invention provides a ligand compound capable of being used for copper catalyzed aryl halide coupling reaction, the ligand compound is a three-class compound containing a 2-(substituted or non-substituted) aminopyridine nitrogen-oxygen group, and the invention also provides a catalytic system for the aryl halide coupling reaction. Thecatalytic system comprises a copper catalyst, a compound containing a 2-(substituted or non-substituted) aminopyridine nitrogen-oxygen group adopted as a ligand, alkali and a solvent, and meanwhile, the invention also provides a system for the aryl halide coupling reaction adopting the catalyst system. The compound containing the 2-(substituted or non-substituted) aminopyridine nitrogen oxygen group can be used as the ligand for the copper catalyzed aryl chloride coupling reaction, and the ligand is stable under a strong alkaline condition and can well maintain catalytic activity when being used for the copper-catalyzed aryl chloride coupling reaction. In addition, the copper catalyst adopting the compound as the ligand can particularly effectively promote coupling of copper catalyzed aryl chloride and various nucleophilic reagents which are difficult to generate under conventional conditions, C-N, C-O and C-S bonds are generated, and numerous useful small molecule compounds are synthesized. Therefore, the aryl halide coupling reaction has a very good large-scale application prospect by adopting the copper catalysis system of the ligand.
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Paragraph 0047; 0053-0056; 0058
(2021/05/29)
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- CuI/2-Aminopyridine 1-Oxide Catalyzed Amination of Aryl Chlorides with Aliphatic Amines
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A class of 2-aminopyridine 1-oxides are discovered to be effective ligands for the Cu-catalyzed amination of less reactive (hetero)aryl chlorides. A wide range of functionalized (hetero)aryl chlorides reacted with various aliphatic amines to afford the desired products in good to excellent yields under the catalyst of CuI/2-aminopyridine 1-oxides. Furthermore, the catalyst system worked well for the coupling of cyclic secondary amines and N-methyl benzylamine with (hetero)aryl chlorides.
- Chen, Xiahong,He, Yongqiang,Liang, Yun,Liu, Wenjie,Wang, Deping,Xia, Xiaohong,Xu, Jiamin,Xu, Zhifeng,Zhang, Fuxing,Zhang, Xin
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supporting information
p. 7486 - 7490
(2020/10/12)
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- Tandem Condensation/Rearrangement Reaction of 2-Aminohetarene N-Oxides for the Synthesis of Hetaryl Carbamates
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A new approach to hetaryl carbamates through a tandem condensation/rearrangement reaction of 2-aminohetarene N-oxides was developed. The developed reaction is suitable for both five- and six-membered heterocycles and proceeds through the condensation of 2
- Bystrov, Dmitry M.,Zhilin, Egor S.,Fershtat, Leonid L.,Romanova, Anna A.,Ananyev, Ivan V.,Makhova, Nina N.
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supporting information
p. 3157 - 3163
(2018/08/24)
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- Gold-catalyzed redox synthesis of imidazo[1,2-a]pyridines using pyridine N-oxide and alkynes
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A mild, catalytic, atom economical synthesis of imidazo[1,2-a]pyridines has been developed: catalytic dichloro(2-pyridinecarboxylato)gold [PicAuCl 2] in the presence of an acid produces a range of imidazo[1,2-a]pyridines in good yields starting
- Talbot, Eric P. A.,Richardson, Melodie,McKenna, Jeffrey M.,Toste, F. Dean
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supporting information
p. 687 - 691
(2014/04/03)
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- Base catalyzed rearrangement of 5-cyanomethyl-2-isoxazolines; novel pathway for the formation of 2-aminopyridine N-oxides
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2-Aminopyridine N-oxides are readily prepared by the base catalyzed rearrangement of 5-cyanomethyl-2-isoxazolines.
- Chucholowski,Uhlendorf
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p. 1949 - 1952
(2007/10/02)
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- Cosmetic composition for imparting to human skin a coloration resembling a natural tan
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A cosmetic composition for imparting to human skin after exposure to sunlight a coloration resembling a natural tan comprising a cosmetic vehicle suitable for topical application to the skin and an effective amount of at least one compound of the formula STR1 wherein R1 represents hydrogen or amino; R2 represents hydrogen, lower alkyl or amino; R3 represents hydrogen, lower alkyl or amino; R4 represents hydrogen, lower alkyl or chlorine; and R5 represents hydrogen, lower alkyl or hydroxy, or amino when R1 is amino, with the proviso that R1, R2 and R3 are not simultaneously amino; and at least one of R1, R2 R3 means amino or an acid addition salt thereof.
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