Synlett, Inhaltsverzeichnis Synlett 2023; 34(19): 2346-2350DOI: 10.1055/a-2159-4847 letter Trimethylsilyl Azide Promoted Shono Oxidation of N,N-Dialkyl Amides Wenlin Luo a Department of Chemistry, Nanchang University, Nanchang, 330031, P. R. of China , Ruixing Zhang a Department of Chemistry, Nanchang University, Nanchang, 330031, P. R. of China , Qi Xu b Nursing School of Nanchang University, Nanchang, 330031, P. R. of China , Shengyu Zheng c Institute for Advanced Study, Nanchang University, Nanchang, 330031, P. R. of China , Junpeng Yang a Department of Chemistry, Nanchang University, Nanchang, 330031, P. R. of China , Meixia Liu a Department of Chemistry, Nanchang University, Nanchang, 330031, P. R. of China , Shengmei Guo ∗ a Department of Chemistry, Nanchang University, Nanchang, 330031, P. R. of China , Hu Cai∗ a Department of Chemistry, Nanchang University, Nanchang, 330031, P. R. of China › Institutsangaben Artikel empfehlen Abstract Artikel einzeln kaufen Alle Artikel dieser Rubrik Abstract An alkoxylation of N,N-dialkyl amides by the Shono reaction has been developed that offers a simple and efficient way to access N-adjacent-carbon-substituted amides. TMSN3 plays an essential role in this transformation and permits the reaction to proceed with a broad substrate scope under mild conditions. This reaction proceeds at a lower current compared with the classical method and it affords the products in up to 91% yield. A possible mechanism is proposed based on control experiments. Key words Key wordstrimethylsilyl azide - Shono oxidation - alkoxylation - amides - electrochemistry - radical relay reaction Volltext Referenzen References and Notes 1a Seavill PW, Wilden JD. Green Chem. 2020; 22: 7737 1b Kärkäs MD. Chem. Soc. Rev. 2018; 47: 5786 1c de Figueiredo RM, Suppo J.-S, Campagne J.-M. Chem. Rev. 2016; 116: 12029 2a Jain P, Verma P, Xia G, Yu J.-Q. Nat. 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The residue was purified by silica gel column chromatography with petroleum ether/ethyl acetate as the eluent (Petroleum ether (PE)/EA = 2:1 to afford the corresponding product 3a as a colorless liquid, 91% yield. 1H NMR (400 MHz, CDCl3) δ 7.43–7.34 (m, 5 H), 4.91–4.52 (m, 2 H), 3.35–2.93 (m, 6 H); 13C NMR (101 MHz, CDCl3) δ 171.35, 131.51, 129.00, 124.39, 82.42, 55.22, 33.10. HRMS (ESI): m/z calcd for C10H13O2NNa [M+Na]+: 202.0844, found: 202.0839. Zusatzmaterial Zusatzmaterial Supporting Information
