Ultrasound-Assisted, Transition-Metal-Free Synthesis of Diaryl Tellurides from Aryl Boronic Acids: A Possible Free-Radical Mechanism

Abstract

The first rapid, catalyst-free synthesis of diphenyl tellurides from readily available diphenyl ditelluride and aryl boronic acids is reported. The high efficiency, general applicability and wide substrate scope, including heterocycles and other functional groups, make this method superior. The technique, which utilizes dimethyl sulfoxide solvent and ultrasound promotion, opens the door for the synthesis of diphenyl tellurides at 100 °C in air within a short time in high yields.

Key words

arylation - cross-coupling - free radicals - diphenyl telluride - transition metals

• References and Notes

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• 11 General Description: Reagents were purchased from Aldrich Chemical Co., TCI and Strem Chemical Co. and were used as received. Reaction products were analyzed by GC-MS (Shimadzu-QP2010 SE), ¹H NMR and ¹³C NMR (Varian Mercury Plus, 300 MHz). Chemical shift values are recorded as parts per million relative to tetramethylsilane as internal standard, unless otherwise indicated, and coupling constants are given in Hertz. A Fisher Scientific Sonic Dismembrator (model 500, 230 V, 50/60 Hz) was used for ultrasonication. Cross-Coupling Reaction; General Procedure: Diphenyl ditelluride (0.12 mmol, 50 mg) and phenylboronic acid (0.27 mmol, 32 mg) were dissolved in DMSO (3 mL) followed by ultrasonication at 100 °C until color change from dark-orange to light-yellow (sometimes colorless) was observed. After usual work up, the crude product was analyzed by GC-MS and then purified by silica gel column chromatography. The purified products were characterized by ¹H and ¹³C NMR spectroscopy. All synthesized compounds are known and their spectroscopic data were consistent with reported values. 4-Methoxyphenyl Phenyl Telluride: ^{6a 1}H NMR (300 MHz, CDCl₃): δ = 7.72 (d, J = 9 Hz, 2 H), 7.59–7.56 (m, 2 H), 7.21–7.17 (m, 3 H), 6.82 (d, J = 8.7 Hz, 2 H), 3.80 (s, 3 H); ¹³C NMR (75 MHz, CDCl₃): δ = 160.0, 141.3, 136.6, 129.5, 127.4, 115.8, 115.7, 103.2, 55.3. Diphenyl Telluride: ^{10 1}H NMR (300 MHz, CDCl₃): δ = 7.71 (d, J = 6.6 Hz, 4 H), 7.35–7.19 (m, 6 H); ¹³C NMR (75 MHz, CDCl₃): δ = 138.2, 129.7, 128.1, 114. 4-Tolyl Phenyl Telluride: ^{6b 1}H NMR (300 MHz, CDCl₃): δ = 7.64 (d, J = 7.8 Hz, 3 H), 7.29–7.17 (m, 4 H), 7.07 (d, J = 7.5 Hz, 2 H), 2.35 (s, 3 H); ¹³C NMR (75 MHz, CDCl₃): δ = 138.9, 137.5, 137.4, 130.6, 129.7, 127.7, 115.4, 110.5, 21.5. 4-Trifluoromethyl Phenyl Phenyl Telluride: ^{5d 1}H NMR (300 MHz, CDCl₃): δ = 7.82 (m, 2 H), 7.68 (m, 2 H), 7.42 (m, 3 H), 7.28 (m, 2 H); ¹³C NMR (75 MHz, CDCl₃): δ = 139.6, 138.2, 136.6, 130.0, 129.7, 128.9, 126.1 (q), 122.3,113.5. 4-Cyanophenyl Phenyl Telluride: ^{5d 1}H NMR (300 MHz, CDCl₃): δ = 7.85–7.82 (m, 2 H), 7.56 (d, J = 8.4 Hz, 2 H), 7.42–7.29 (m, 5 H); ¹³C NMR (75 MHz, CDCl₃): δ = 140.3, 135.9, 132.4, 130.0, 129.4, 124.5, 118.9, 113.0, 110.8. 4-Fluorophenyl Phenyl Telluride: ^{6b 1}H NMR (300 MHz, CDCl₃): δ = 7.74–7.63 (m, 4 H), 7.31–7.19 (m, 3 H), 6.99–6.90 (m, 2 H); ¹³C NMR (75 MHz, CDCl₃): δ = 164.9, 161.6, 140.7, 138.2, 132.1, 129.8, 129.7, 128.0, 117.0, 114.8. 2-Naphthyl Phenyl Telluride: ^{6b 1}H NMR (300 MHz, CDCl₃): δ = 8.25 (d, J = 6.3 Hz, 1 H), 7.82–7.66 (m, 7 H), 7.49–7.45 (m, 2 H), 7.32–7.19 (m, 3 H); ¹³C NMR (75 MHz, CDCl₃): δ = 138.1, 138.0, 137.9, 134.9, 134.5, 132.8, 129.7, 128.8, 128.0, 127.9, 127.6, 126.6, 126.5, 115.0, 112.2. 4-Ethoxycarbonylphenyl Phenyl Telluride: ^{6b 1}H NMR (300 MHz, CDCl₃): δ = 7.80 (m, 3 H), 7.62 (d, J = 8.1 Hz, 2 H), 7.40–7.25 (m, 4 H), 4.33 (q, J = 6.9, 7.2 Hz, 2 H), 1.37 (t, J = 7.2 Hz, 3 H); ¹³C NMR (75 MHz, CDCl₃): δ = 166.6, 139.5, 136.2, 130.2, 130.0, 129.7, 128.8, 123.1, 113.7, 61.1, 14.5. 3-Thiophenyl Phenyl Telluride: ^{6b 1}H NMR (300 MHz, CDCl₃): δ = 7.72–7.70 (m, 1 H), 7.61–7.57 (m, 3 H), 7.31–7.16 (m, 4 H); ¹³C NMR (75 MHz, CDCl₃): δ = 138.2, 137.0, 136.9, 136.7, 134.7, 129.7, 129.6, 128.0, 127.7, 127.4, 115.4, 104.0.