- Synthesis of 3-Fluoropyridines via Photoredox-Mediated Coupling of α,α-Difluoro-β-iodoketones with Silyl Enol Ethers
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A method for the synthesis of diversely substituted 3-fluoropyridines from two ketone components is described. The reaction involves photoredox coupling of α,α-difluoro-β-iodoketones with silyl enol ethers catalyzed by fac-Ir(ppy)3 under blue LED irradiation with subsequent one-pot condensation with ammonium acetate. Based on cyclic voltammetry studies, it was determined that α,α-difluoro-β-iodoketones are reduced notably easier compared to 2,2,2-trifluoro-1-iodoethane, which may be ascribed to the influence of the carbonyl group.
- Scherbinina, Sofya I.,Fedorov, Oleg V.,Levin, Vitalij V.,Kokorekin, Vladimir A.,Struchkova, Marina I.,Dilman, Alexander D.
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- Synthesis of β-nitro ketones from geminal bromonitroalkanes and silyl enol ethers by visible light photoredox catalysis
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Various β-nitro ketones, including those bearing a β-tertiary carbon, were prepared from geminal bromonitroalkanes and trimethylsilyl enol ethers of a broad range of ketones by visible light photoredox catalysis, which were then easily converted into β-amino ketones, 1,3-amino alcohols, α,β-unsaturated ketones, β-cyano ketones and γ-nitro ketones.
- Cao, Haoying,Ma, Shanshan,Feng, Yanhong,Guo, Yawen,Jiao, Peng
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supporting information
p. 1780 - 1783
(2022/02/17)
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- Versatile and base-free copper-catalyzed α-arylations of aromatic ketones using diaryliodonium salts
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A ligand and base-free copper catalyzed synthetic method for the efficient α-arylation of aromatic ketones is described. In order to avoid strong bases, ketone-derived silyl enol ethers were employed. Their reaction with diaryliodonium salts as aryl source provided the intermolecular C–C coupling displaying good functional group tolerance and requiring low catalyst loading.
- Bouquin, Maxime,Jaroschik, Florian,Taillefer, Marc
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supporting information
(2021/06/11)
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- Direct synthesis of 2-arylazulenes by [8+2] cycloaddition of 2: H -cyclohepta [b] furan-2-ones with silyl enol ethers
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We developed a procedure for the direct synthesis of 2-arylazulenes, which were obtained in moderate to excellent yields, by [8+2] cycloaddition of 2H-cyclohepta[b]furan-2-ones with aryl-substituted silyl enol ethers. The structures of some 2-arylazulenes were clarified by single-crystal X-ray analysis. The 2-phenylazulene derivatives obtained by this study showed noticeable fluorescence in acidic media.
- Shoji, Taku,Sugiyama, Shuhei,Kobayashi, Yoshiaki,Yamazaki, Akari,Ariga, Yukino,Katoh, Ryuzi,Wakui, Hiroki,Yasunami, Masafumi,Ito, Shunji
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supporting information
p. 1485 - 1488
(2020/02/13)
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- Photoredox-Catalyzed Generation of Sulfamyl Radicals: Sulfonamidation of Enol Silyl Ether with Chlorosulfonamide
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A novel and practical photoredox-catalyzed generation of sulfamyl radicals followed by radical sulfonamidation of enol silyl ether has been described. Diverse functionalized β-ketosulfonamides were prepared in modest to excellent yields under mild and economic reaction conditions through the present catalytic protocol. Furthermore, the methodology developed provides an efficient and convenient approach to the synthesis of the antiseizure drug Zonisamide.
- Luo, Qiyu,Mao, Runyu,Zhu, Yan,Wang, Yonghui
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p. 13897 - 13907
(2019/11/11)
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