Tetrabutylammonium Iodide-Promoted Acyloxylation–Peroxidation of Alkenes with Carboxylic Acid and tert-Butyl Hydroperoxide

Abstract

An efficient synthesis of tert-butyl peroxides through TBAI-promoted acyloxylation–peroxidation of alkenes by using a carboxylic acid and tert-butyl hydroperoxide was developed. The synthetic utility of our method is enhanced by simple manipulations, easily available starting materials, and a wide substrate scope.

Key words

tetrabutylammonium iodide - acyloxylation - peroxidation - alkenes - carboxylic acids - butyl hydroperoxide

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• 13 1-[(tert-Butylperoxy)methyl]-2-(methoxycarbonyl)ethyl 4-tert-Butylbenzoate (3a); Typical Procedure A test tube was charged with TBAI (36.9 mg, 0.1 mmol) and 4-tert-butylbenzoic acid (35.6 mg, 0.2 mmol). DMSO (1.0 mL), methyl acrylate (2a; 1.6 mmol), and a 70% aq solution of TBHP (180.2 mg, 1.4 mmol) were added from a syringe, and the mixture was stirred at 80 °C for 12 h under air. The reaction was then quenched with sat. aq Na₂SO₃ to remove residual TBHP. Evaporation of the solvent followed by flash column chromatography (silica gel, PE–EtOAc) gave a colorless liquid; yield: 53.5 mg (76%). ¹H NMR (400 MHz, CDCl₃): δ = 8.09–8.02 (m, 2 H), 7.51–7.43 (m, 2 H), 5.58 (dd, J = 5.9, 3.5 Hz, 1 H), 4.42 (qd, J = 13.0, 4.7 Hz, 2 H), 3.77 (d, J = 2.5 Hz, 3 H), 1.34 (s, 9 H), 1.24 (s, 9 H). ¹³C NMR (101 MHz, CDCl₃): δ = 168.6, 165.8, 157.1, 129.9, 126.5, 125.4, 80.8, 73.4, 70.7, 52.5, 35.1, 31.1, 26.2. HRMS (ESI-TOF): m/z [M + Na]⁺ calcd for C₁₉H₂₈NaO₆: 375.1778; found: 375.1770.