- Cu-catalyzed N- and O-arylation of 2-,3-, and 4-hydroxypyridines and hydroxyquinolines
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With use of Cu-based catalysts, 2- and 4-hydroxypyridines were N-arylated in modest to excellent yields. In the case of 2-hydroxypyridine, the use of 4,7-dimethoxy-1,10-phenanthroline, 3, expanded the scope of previous literature reports to include the use of N-containing heteroaryl halides, and 2-substituted aryl halides. In addition, by using a copper catalyst based on 2,2,6,6-tetramethylheptane-3,5-dione, 4, the first N-arylations of 4-hydroxypyridines and O-arylations of 3-hydroxypyridines with aryl bromides and iodides have been accomplished.
- Altman, Ryan A.,Buchwald, Stephen L.
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- Light-induced [2 + 2] cycloadditions for the construction of cyclobutane-fused pyridinyl sulfonyl fluorides
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Cyclobutanes are an important class of motifs present in a wide range of natural products and other biologically significant molecules. A photocatalytic [2 + 2] cycloaddition between pyridones or isoquinolones and ethenesulfonyl fluoride was achieved, providing a portal to a class of unique cyclobutane-fused pyridinyl sulfonyl fluorides with quaternary rigid rings (30 examples). Further applications of these novel sulfonyl fluoride molecules in SuFEx click chemistry were also accomplished, providing the corresponding sulfonates and sulphonamides with reasonable yields.
- Liu, Jing,Wang, Shi-Meng,Qin, Hua-Li
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supporting information
p. 4019 - 4023
(2020/06/09)
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- Rhodium(III)-Catalyzed Annulation of Pyridinones with Alkynes via Double C-H Activation: A Route to Functionalized Quinolizinones
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A Rh(III)-catalyzed oxidative annulation of pyridin-2(1H)-ones with alkynes via double C-H activation to produce highly functionalized 4H-quinolizin-4-ones is disclosed. This reaction features easily available starting materials, simple manipulation, a relatively wide substrate scope, and good functional group tolerance. The application of this protocol is demonstrated by the synthesis of a known fluorescent quinolizino[3,4,5,6-ija]quinolinium salt.
- Li, Juan,Yang, Yudong,Wang, Zhigang,Feng, Boya,You, Jingsong
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supporting information
p. 3083 - 3086
(2017/06/23)
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- N-arylation of pyridin-2(1H)-ones with pentavalent organobismuth reagents under copper-free conditions
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An efficient method for the N-arylation of pyridin-2(1H)-ones and the related heteroaromatic lactams has been established via ligand-coupling reactions using tri- or tetra-aryl organobismuth(V) reagents such as triarylbismuth dichlorides. Also, N-alkenylation of pyridin-2(1H)-one was achieved similarly by using alkenyltriarylbismuth(V) reagents.
- Ikegai, Kazuhiro,Nagata, Yuzo,Mukaiyama, Teruaki
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p. 761 - 767
(2008/02/01)
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- An efficient copper-catalyzed coupling reaction of pyridin-2-ones with aryl and heterocyclic halides based on Buchwald's protocol
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An efficient copper-catalyzed coupling reaction based on the Buchwald's protocol has been established for pyridin-2-ones with aryl iodides, aryl bromides, and heterocyclic bromides.
- Li, Chun Sing,Dixon, Darryl D.
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p. 4257 - 4260
(2007/10/03)
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