Oxidation of Organosulfides to Organosulfones with Trifluoromethyl 3-Oxo-1λ³,2-benziodoxole-1(3H)-carboxylate as an Oxidant

Abstract

An alternative approach is described for the oxidation of organosulfides to the corresponding organosulfones by using trifluoromethyl 3-oxo-1λ³,2-benziodoxole-1(3H)-carboxylate as an oxidant. The oxidation of the sulfides was performed by using 2.4 equivalents of the oxidant in refluxing acetonitrile. The oxidation products were isolated in good to excellent yields.

Key words

oxidation - sulfides - sulfones - hypervalent iodine - oxidizing agents

• References and Notes

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• 31 Sulfones 10a–h; General Procedure A mixture of the appropriate sulfide 9 (0.5 mmol) and benziodoxole 8 (413 mg, 2.4 equiv) in MeCN (3 mL) was refluxed for 16–20 h. When the reaction was complete (TLC), sat. aq NaHCO₃ (5 mL) was added and the mixture was extracted with EtOAc (3 × 15 mL). The organic layers were combined, dried (Na₂SO₄), filtered, and concentrated under vacuum. The crude product was purified by column chromatography [silica gel, EtOAc–hexane (1:3)]. tert-Butyl Phenyl Sulfone (10a) ^22b White solid; yield: 84 mg (0.42 mmol, 85%); mp; 90–92 °C. IR (film): 697, 725, 749, 764, 802, 996, 1021, 1076, 1130, 1277, 1294, 1449, 1475 cm^–1. ¹H NMR (400 MHz, CDCl₃): δ = 1.23 (s, 9 H, t-Bu), 7.46 (t, J = 7.6 Hz, 2 H, ArH), 7.56 (t, J = 7.6 Hz, 1 H, ArH), 7.77 (d, J = 7.6 Hz, 2 H, ArH). ¹³C NMR (100 MHz, CDCl₃): δ = 23.5, 59.7, 128.7, 130.3, 133.6, 135.2. GC/MS: m/z (%) = 198(5), 143(25), 79(13), 77(50), 58(29), 57(100), 51(51), 41(50).
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