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Synlett 2023; 34(19): 2346-2350
DOI: 10.1055/a-2159-4847
DOI: 10.1055/a-2159-4847
letter
Trimethylsilyl Azide Promoted Shono Oxidation of N,N-Dialkyl Amides
Authors
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 reactionSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2159-4847.
- Supporting Information (PDF)
Publication History
Received: 24 June 2023
Accepted after revision: 23 August 2023
Accepted Manuscript online:
23 August 2023
Article published online:
04 October 2023
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- 17 General Procedure for Synthesis of 3<. 3a as an example. 1a (0.4 mmol), nBu4NBF4 (0.4 mmol), and CH3CN: 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 Na2SO4, 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. 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.