Trimethylsilyl Azide Promoted Shono Oxidation of N,N-Dialkyl Amides

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

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.