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.

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

References and Notes

For pioneering studies of decarboxylative cross-coupling reactions, see:

<A NAME="RW08510ST-1A">1a</A> Nilsson M. Acta Chem. Scand.  1958,  12:  537 

<A NAME="RW08510ST-1B">1b</A> Nilsson M. Acta Chem. Scand.  1966,  20:  423 

For reviews, see:

<A NAME="RW08510ST-1C">1c</A> Baudoin O. Angew. Chem. Int. Ed.  2007,  46:  1373 

<A NAME="RW08510ST-1D">1d</A> Gooßen LJ. Rodríguez N. Gooßen K. Angew. Chem. Int. Ed.  2008,  47:  3100 

<A NAME="RW08510ST-1E">1e</A> Gooßen LJ. Gooßen K. Rodríguez N. Blanchot M. Linder C. Zimmermann B. Pure Appl. Chem.  2008,  80:  1725 

<A NAME="RW08510ST-2A">2a</A> Myers AG. Tanaka D. Mannion MR. J. Am. Chem. Soc.  2002,  124:  11250 

<A NAME="RW08510ST-2B">2b</A> Tanaka D. Myers AG. Org. Lett.  2004,  6:  433 

<A NAME="RW08510ST-2C">2c</A> Tanaka D. Romeril SP. Myers AG. J. Am. Chem. Soc.  2005,  127:  10323 

For selected examples, see:

<A NAME="RW08510ST-3A">3a</A> Stephan MS. Teunissen AJJM. Verzijl GKM. de Vries JG. Angew. Chem. Int. Ed.  1998,  37:  662 

<A NAME="RW08510ST-3B">3b</A> Rayabarapu DK. Tunge JA. J. Am. Chem. Soc.  2005,  127:  13510 

<A NAME="RW08510ST-3C">3c</A> Forgione P. Brochu M.-C. St-Onge M. Thesen KH. Bailey MD. Bilodeau F. J. Am. Chem. Soc.  2006,  128:  11350 

<A NAME="RW08510ST-3D">3d</A> Gooßen LJ. Deng G. Levy LM. Science  2006,  313:  662 

<A NAME="RW08510ST-3E">3e</A> Gooßen LJ. Rodríguez N. Melzer B. Linder C. Deng G. Levy LM. J. Am. Chem. Soc.  2007,  129:  4824 

<A NAME="RW08510ST-3F">3f</A> Becht J.-M. Catala C. Le Drian C. Wagner A. Org. Lett.  2007,  9:  1781 

<A NAME="RW08510ST-3G">3g</A> Voutchkova A. Coplin A. Leadbeater NE. Crabtree RH. Chem. Commun.  2008,  6312 

<A NAME="RW08510ST-3H">3h</A> Gooßen LJ. Rodríguez N. Linder C. J. Am. Chem. Soc.  2008,  130:  15248 

<A NAME="RW08510ST-3I">3i</A> Miyasaka M. Fukushima A. Satoh T. Hirano K. Miura M. Chem. Eur. J.  2009,  15:  3674 

<A NAME="RW08510ST-3J">3j</A> Hu P. Kan J. Su WP. Hong MC. Org. Lett.  2009,  11:  2341 

<A NAME="RW08510ST-3K">3k</A> Cornella J. Lu P. Larrosa I. Org. Lett.  2009,  11:  5506 

<A NAME="RW08510ST-3L">3l</A> Wang ZY. Ding QP. He XD. Wu J. Org. Biomol. Chem.  2009,  7:  863 

<A NAME="RW08510ST-3M">3m</A> Shang R. Fu Y. Wang Y. Xu Q. Yu HZ. Liu L. Angew. Chem. Int. Ed.  2009,  48:  9350 

<A NAME="RW08510ST-3N">3n</A> Shang R. Fu Y. Li J.-B. Zhang S.-L. Guo Q.-X. Liu L. J. Am. Chem. Soc.  2009,  131:  5738 

<A NAME="RW08510ST-3O">3o</A> Zhang S.-L. Fu Y. Shang R. Guo Q.-X. Liu L. J. Am. Chem. Soc.  2010,  132:  638 

<A NAME="RW08510ST-3P">3p</A> Gooßen LJ. Rodríguez N. Lange PP. Linder C. Angew. Chem. Int. Ed.  2010,  49:  1111 

<A NAME="RW08510ST-3Q">3q</A> Yamashita M. Hirano K. Satoh T. Miura M. Org. Lett.  2010,  12:  592 

<A NAME="RW08510ST-3R">3r</A> Shang R. Xu Q. Jiang Y.-Y. Wang Y. Liu L. Org. Lett.  2010,  12:  1000 

<A NAME="RW08510ST-3S">3s</A> Xie K. Yang Z. Zhou X. Li X. Wang S. Tan Z. An X. Guo C.-C. Org. Lett.  2010,  12:  1564 

<A NAME="RW08510ST-3T">3t</A> Zhang F. Greaney MF. Angew. Chem. Int. Ed.  2010,  49:  2768 

<A NAME="RW08510ST-4">4</A> Zhang B. Salituro G. Szalkowski D. Li Z. Zhang Y. Royo I. Vitella D. Diez MT. Pelaez F. Ruby C. Kendall RL. Mao X. Griffin P. Calaycay J. Zierath JR. Heck JV. Smith RG. Moller DE. Science  1999,  284:  974 

<A NAME="RW08510ST-5A">5a</A> Kvalnes DE. J. Am. Chem. Soc.  1934,  56:  2478 

<A NAME="RW08510ST-5B">5b</A> Higuchi T. Satake C. Hirobe M. J. Am. Chem. Soc.  1995,  117:  8879 

<A NAME="RW08510ST-5C">5c</A> Zhang HB. Liu L. Chen YJ. Wang D. Li C.-J. Adv. Synth. Catal.  2006,  348:  229 

<A NAME="RW08510ST-6">6</A>

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.

<A NAME="RW08510ST-7A">7a</A> Gooßen LJ. Linder C. Rodríguez N. Lange PP. Fromm A. Chem. Commun.  2009,  7173 

<A NAME="RW08510ST-7B">7b</A> Cornella J. Sanchez C. Banawa D. Larrosa I. Chem. Commun.  2009,  7176 

<A NAME="RW08510ST-7C">7c</A> Lu P. Sanchez C. Cornella J. Larrosa I. Org. Lett.  2009,  11:  5710