Synthesis of Aryl-Substituted 1,4-Benzoquinone via Palladium(II)-Catalyzed Decarboxylative Coupling of Arene Carboxylate with 1,4-Benzoquinone

Abstract

Various aryl-substituted 1,4-benzoquinone derivatives have been prepared via a palladium-catalyzed decarboxylative cross-coupling of electron-rich aromatic acids with 1,4-benzoquinones.

Key words

palladium-catalysis - decarboxylative coupling - C-C bond formation - arene carboxylate - benzoquinone

References and Notes

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6

Representative Procedure 2,6-Dimethoxybenzoic acid (36 mg, 0.2 mmol, 1.0 equiv), 1,4-benzoquinone (32 mg, 0.3 mmol, 1.5 equiv), Pd(OAc)₂ (9 mg, 0.04 mmol, 0.02 equiv), and Ag₂CO₃ (165 mg, 0.6 mmol, 3 equiv) were added in DMF (10 mL) and DMSO (0.5 mL). The mixture was heated at 120 ˚C for 3 h, then was cooled and poured into EtOAc (50 mL). The mixture was filtered; the filtrate was washed sequentially with aq HCl (1 M, 2 × 40 mL) and brine (20 mL), then was dried over MgSO₄, filtered, and concentrated. Chromatographic separation gave the pure product 1 (40 mg, 0.164 mmol, 83%). ^¹H NMR (400 MHz, CDCl₃): δ = 7.33 (t, J = 8.4 Hz, 1 H), 6.85 (d, J = 10.0 Hz, 1 H), 6.81-6.71 (m, 2 H), 6.61 (d, J = 8.4 Hz, 2 H), 3.73 (s, 6 H). ^¹³C NMR (100 MHz, CDCl₃): δ = 187.80, 185.54, 157.80, 142.73, 137.13, 136.32, 135.99, 130.89, 110.03, 103.96, 55.83. MS (EI): m/z (%) = 244 (100) [M⁺], 213 (22), 162 (56), 161 (54), 131 (35), 91 (39), 54 (60), 39 (29). ESI-HRMS: m/z calcd for C₁₄H₁₂O₄ [M + H]⁺: 245.0808; found: 245.0803, error: 2.0 ppm.