- Manganese(III)-Promoted Double Carbonylation of Anilines Toward α-Ketoamides Synthesis
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Employing anilines as nucleophiles in double carbonylation is a longstanding challenge. In this communication, a Mn(III)-promoted double carbonylation of alkylborates or Hantzsch esters with anilines toward the synthesis of α-ketoamides has been developed. By using easily available potassium alkyltrifluoroborates or Hantzsch esters as the starting material, and cheap and non-toxic Mn(OAc)3 ? 2H2O as the promotor, a broad range of alkyl α-ketoamide derivatives were synthesized in moderate to good yields with excellent selectivity. (Figure presented.).
- Chen, Bo,Kuai, Chang-Sheng,Wu, Xiao-Feng,Xu, Jian-Xing
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supporting information
(2021/12/06)
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- Asymmetric Transfer Hydrogenation of α-Keto Amides; Highly Enantioselective Formation of Malic Acid Diamides and α-Hydroxyamides
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The asymmetric transfer hydrogenation (ATH) of α-keto-1,4-diamides using a tethered Ru/TsDPEN catalyst was achieved in high ee. Studies on derivatives identified the structural elements which lead to the highest enantioselectivities in the products. The α-keto-amide reduction products have been converted to a range of synthetically valuable derivatives.
- Gediya, Shweta K.,Vyas, Vijyesh K.,Clarkson, Guy J.,Wills, Martin
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supporting information
p. 7803 - 7807
(2021/10/20)
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- Visible-light initiated copper(i)-catalysed oxidative C-N coupling of anilines with terminal alkynes: One-step synthesis of α-ketoamides
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Development of C-N coupling processes is fundamentally important and challenging for the synthesis of biologically active molecules and drugs. Herein, we report a highly atom efficient green process for the synthesis of α-ketoamides via visible-light induced copper(i) chloride catalysed direct oxidative Csp-N coupling reactions using commercially available alkynes and anilines at room temperature without the use of hazardous chemicals and harsh reaction conditions. Forty-seven examples are presented using a broad range of substrates including electron deficient anilines and various terminal alkynes. The current photochemical process is able to achieve epoxide hydrolase inhibitors in one step with high yield (92-95%). This transformation is highly efficient and highly selective for the synthesis of α-ketoamides. This journal is
- Sagadevan, Arunachalam,Ragupathi, Ayyakkannu,Lin, Chun-Cheng,Hwu, Jih Ru,Hwang, Kuo Chu
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supporting information
p. 1113 - 1119
(2015/03/04)
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- Iodine-mediated oxidation of ynamides: A facile access to N-monosubstituted α-ketoamides and α-ketoimides
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An efficient iodine-mediated oxidation reaction for ynamides has been developed to produce N-monosubstituted α-ketoamides and α-ketoimides. This oxidative method, which exhibits good functional group tolerance, was performed under mild conditions without a metal catalyst.
- Huang, Hai,He, Guangke,Zhu, Xiaolin,Jin, Xiaodong,Qiu, Shineng,Zhu, Hongjun
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p. 7174 - 7183
(2015/01/16)
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- Syntheses of Dialkyl and Functionalized Ketones via 1-(Benzotriazol-1-yl)alkyl Methyl Thioethers
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Benzotriazol-1-ylmethyl methyl thioether (1), after easy deprotonation by BuLi, reacted with alkyl halides to afford 1-(benzotriazol-1-yl)alkyl methyl thioethers 2 in good yields. The utility of compounds 2 as alkanoyl anion equivalents was demonstrated by the reactions of their anions with alkyl halides, aldehydes, ketones, esters, and phenyl isocyanate: the products were readily hydrolyzed to α-functionalized ketones in dilute aqueous acid.
- Katritzky, Alan R.,Oniciu, Daniela C.,Ghiviriga, Ion,Soti, Ferenc
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p. 2110 - 2115
(2007/10/03)
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- Substituted (Carbazol-9-yl)(benzotriazol-1-yl)methanes: Novel Acyl Anion Equivalents
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Alkyl(carbazol-9-yl)(benzotriazol-1-yl)methanes are deprotonated by BuLi to form anions which react with alkyl halides, aldehydes, and isocyanates to afford the expected products and which add 1,4 to α,β-unsaturated ketones.These products are hydrolyzed by dilute acid at ambient temperature to afford the corresponding ketones.
- Katritzky, Alan R.,Yang, Zhijun,Lam, Jamshed N.
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p. 6917 - 6923
(2007/10/02)
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