Palladium-Catalyzed Oxidative Allylic Alkylation of N-Hydroxy­imides

^◊ The authors contributed equally to the project

Abstract

A palladium-catalyzed oxidative C–H allylic alkylation of N-hydroxyimides has been developed. This transformation provided valuable N-allyloxypyrrolidinediones in moderate to excellent yields using operationally simple, ligand free, and mild reaction conditions. The reaction tolerated broad and variable substituents on allylarenes and N-hydroxyimides.

Key words

allylic C–H activation - palladium - N-hydroxyimides - C–O bond formation

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• 19 General Procedure for C–H Activation/C–O Bond Formation To a solution of aryl benzene 1 (0.1 mmol, 1 equiv) in acetonitrile (2 mL) were added N-hydroxyimide (2, 3.0 equiv), copper(II) acetate monohydrate (1.0 equiv), acetic acid (0.5 equiv), and Pd(OAc)₂ (0.1 equiv) in the same order and heated at 75 °C. The reaction was conducted in a round-bottom flask equipped with a reflux condenser. After 24–28 h, the reaction mass was dried on a small mass of silica and was purified by flash chromatography using hexanes/EtOAc . (E)-1-[(3-(4-Methoxyphenyl)allyl)oxy]pyrrolidine-2,5-dione (3a) Prepared according to the general procedure. Purification by column chromatography (n-hexane/EtOAc, 4:1) gave 3a in 84% yield as a white solid (mp 98–100 °C). ¹H NMR (400 MHz, CDCl₃): δ = 7.34–7.30 (d, J = 8.6 Hz, 2 H), 6.87–6.84 (d, J = 8.7 Hz, 2 H), 6.60 (d, J = 15.9 Hz, 1 H), 6.25–6.18 (dt, J = 15.8, 7.3 Hz, 1 H), 4.77 (dd, J = 7.3, 1.0 Hz, 2 H), 3.80 (s, 3 H), 2.65 (s, 4 H). ¹³C NMR (100 MHz, CDCl₃): δ = 171.5, 160.0, 137.5, 128.4, 128.2, 119.2, 114.1, 77.7, 55.3, 25.4. HRMS: m/z calcd for C₁₄H₁₆NO₄ [M + H⁺]: 261.1001; found: 261.1066.