Synthesis 2013; 45(17): 2387-2390
DOI: 10.1055/s-0033-1339470
practical synthetic procedures
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Aryl Ethers from Aromatic Carboxylic Acids

Sukalyan Bhadra
Department of Chemistry, Organic Chemistry, Technische Universität Kaiserslautern, Erwin-Schrödinger-Straße, 67663 Kaiserslautern, Germany   Fax: +49(631)2053921   Email: [email protected]
,
Wojciech I. Dzik
Department of Chemistry, Organic Chemistry, Technische Universität Kaiserslautern, Erwin-Schrödinger-Straße, 67663 Kaiserslautern, Germany   Fax: +49(631)2053921   Email: [email protected]
,
Lukas J. Gooßen*
Department of Chemistry, Organic Chemistry, Technische Universität Kaiserslautern, Erwin-Schrödinger-Straße, 67663 Kaiserslautern, Germany   Fax: +49(631)2053921   Email: [email protected]
› Author Affiliations
Further Information

Publication History

Received: 14 June 2013

Accepted: 21 June 2013

Publication Date:
15 July 2013 (online)


Abstract

A silver/copper bimetallic catalyst system promotes the decarboxylative Chan–Evans–Lam alkoxylation of ortho-substituted aromatic carboxylate salts with tetraalkyl orthosilicates or triaryl borates. Non-ortho-substituted carboxylates are alkoxylated via an ortho-C–H-alkoxylation with concomitant cleavage of the carboxylate directing group via protodecarboxylation. This way, meta-substituted carboxylates are converted into para-substituted alkoxyarenes and vice versa. The combined processes provide a convenient synthetic entry to the important class of aromatic ethers from widely available carboxylic acids.

Supporting Information

 
  • References

  • 2 March J. Advanced Organic Chemistry . Wiley-Interscience; Hoboken: 1992

    • For reviews, see:
    • 3a Hartwig JF. Nature 2008; 455: 314
    • 3b Ley SV, Thomas AW. Angew. Chem. Int. Ed. 2003; 42: 5400 ; Angew. Chem. 2003, 115, 5558
    • 4a Chan DM. T, Monaco KL, Wang R.-P, Winters MP. Tetrahedron Lett. 1998; 39: 2933
    • 4b Evans DA, Katz JL, West TR. Tetrahedron Lett. 1998; 39: 2937
    • 4c Lam PY. S, Clark CG, Saubern S, Adams J, Winters MP, Chan DM. T, Combs A. Tetrahedron Lett. 1998; 39: 2941
  • 5 For a review on this topic, see: Qiao JX, Lam PY. S. Synthesis 2011; 829

    • For reviews on decarboxylative couplings, see:
    • 6a Goossen LJ, Rodríguez N, Goossen K. Angew. Chem. Int. Ed. 2008; 47: 3100 ; Angew. Chem. 2008, 120, 3144
    • 6b Goossen LJ, Collet F, Goossen K. Isr. J. Chem. 2010; 50: 617
    • 6c Rodríguez N, Goossen LJ. Chem. Soc. Rev. 2011; 40: 5030
    • 6d Shang R, Liu L. Sci. China Chem. 2011; 54: 1670
    • 6e Dzik WI, Lange PP, Goossen LJ. Chem. Sci. 2012; 3: 2671
    • 7a Goossen LJ, Deng G, Levy LM. Science 2006; 313: 662
    • 7b Goossen LJ, Rodríguez N, Linder C. J. Am. Chem. Soc. 2008; 130: 15248
    • 7c Rudolphi F, Song B, Goossen LJ. Adv. Synth. Catal. 2011; 353: 337
  • 8 Bhadra S, Dzik WI, Goossen LJ. J. Am. Chem. Soc. 2012; 134: 9938
  • 9 Bhadra S, Dzik WI, Goossen LJ. Angew. Chem. Int. Ed. 2013; 52: 2959 ; Angew. Chem. 2013, 125, 3031
  • 10 Milton EJ, Fuentes JA, Clarke ML. Org. Biomol. Chem. 2009; 7: 2645
    • 11a Goossen LJ, Linder C, Rodríguez N, Lange PP, Fromm A. Chem. Commun. 2009; 7173
    • 11b Cornella J, Sanchez C, Banawa D, Larrosa I. Chem. Commun. 2009; 7176
    • 11c Goossen LJ, Rodríguez N, Linder C, Lange PP, Fromm A. ChemCatChem 2010; 2: 430
  • 12 For an overview on carboxylate directed C–H functionalizations of arenes, see: Satoh T, Miura M. Synthesis 2010; 3395

    • Examples of carboxylate directed C–H hydroxylations:
    • 13a Zhang Y.-H, Yu J.-Q. J. Am. Chem. Soc. 2009; 131: 14654
    • 13b Makhlynets OV, Das P, Taktak S, Flook M, Mas-Ballesté R, Rybak-Akimova EV, Que Jr. L. Chem. Eur. J. 2009; 15: 13171
    • 14a Goossen LJ, Thiel WR, Rodríguez N, Linder C, Melzer B. Adv. Synth. Catal. 2007; 349: 2241
    • 14b Goossen LJ, Manjolinho F, Khan BA. J. Org. Chem. 2009; 74: 2620