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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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 Ag2 CO3 (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%). ¹ H
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). ¹³ C 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 C14 H12 O4 [M + H]+ : 245.0808;
found: 245.0803, error: 2.0 ppm.
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