Synlett 2023; 34(19): 2346-2350
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
,
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 We thank the National Science Foundation of China (21861024) for financial support.
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
trimethylsilyl azide -
Shono oxidation -
alkoxylation -
amides -
electrochemistry -
radical relay reaction
Supporting Information
Supporting information for this article is available online at https://doi.org/10.1055/a-2159-4847.
Supporting Information
Publikationsverlauf
Eingereicht: 24. Juni 2023
© 2023. Thieme. All rights reserved
Georg Thieme Verlag KG
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17 General Procedure for Synthesis of 3< . 3a as an example. 1a (0.4 mmol), n Bu4 NBF4 (0.4 mmol), and CH3 CN: MeOH (5.0 mL/5.0 mL) were added into an oven-dried three-necked flask (25 mL) with a stir bar. The flask was equipped with platinum electrodes (10 × 10 × 0.3 mm3 ) as the cathode and anode. The reaction mixture was stirred and electrolyzed at a constant current of 10 mA and air atmosphere under room temperature for 6 h. The mixture was washed with NaCl solution and then was extracted by EA. The combined organic phase was dried over anhydrous Na2 SO4 , filtered, and concentrated under reduced pressure. 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. 1 H 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); 13 C 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 C10 H13 O2 NNa [M+Na]+ : 202.0844, found: 202.0839.
