Download PDF
Synthesis 2010(24): 4268-4272  
DOI: 10.1055/s-0030-1258965
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Copper-Catalyzed Hydroxylation of Aryl Halides with Tetrabutylammonium Hydroxide: Synthesis of Substituted Phenols and Alkyl Aryl Ethers

Rajesh Paul, Md Ashif Ali, Tharmalingam Punniyamurthy*
Department of Chemistry, Indian Institute of Technology Guwahati, Guwahati 781039, India
Fax: +91(361)2690762; e-Mail: tpunni@iitg.ernet.in;
Further Information

Publication History

Received 19 July 2010
Publication Date:
09 November 2010 (online)

    Permissions and Reprints All articles of this category

Abstract

The selective hydroxylation of aryl iodides and aryl bromides with tetrabutylammonium hydroxide pentahydrate is described. For this, the combination of copper(I) iodide and 8-hydroxyquinaldine at 70-130 ˚C in a mixture of dimethyl sulfoxide and water (2:3) is used. The resultant phenols can be readily reacted with alkyl and allyl halides in situ to provide the corresponding alkyl or allyl aryl ethers in high yields. The reactions are simple, general, and efficient, affording substituted phenols and alkyl aryl ethers under aerobic conditions.

Key words

phenols - copper iodide - tetrabutylammonium hydroxide pentahydrate - aryl halides - hydroxylation

    References

  • 1a Tyman JHP. Synthetic and Natural Phenols   Elsevier; Amsterdam: 1996. 
    Google Scholar
  • 1b Rappoport Z. The Chemistry of Phenols   Wiley; Weinheim: 2003. 
    Google Scholar
  • 1c Hartwig JF. In Handbook of Organopalladium Chemistry for Organic Synthesis   Negishi E.-i. Wiley-Interscience; New York: 2002. 
    Google Scholar
  • 1d Kotschy A. Timári G. Heterocycles from Transition Metal Catalysis   Springer; Dordrecht: 2005. 
    Google Scholar
  • 2a Guo Z. Schultz AG. Org. Lett.  2001,  3:  1177 
    Google Scholar
  • 2b Schultz AG. Hardinger SA. J. Org. Chem.  1991,  56:  1105 
    Google Scholar
  • 2c Gevorgyan V. Quan LG. Yamamoto Y.
    J. Org. Chem.  1998,  63:  1244 
    Google Scholar
  • 2d Lefebvre O. Brigaud T. Portella C. Tetrahedron  1998,  54:  5939 
    Google Scholar
  • 2e Yamamoto Y. Nunokawa K. Ohno M. Eguchi S. Synthesis  1996,  949 
    Google Scholar
  • 2f Harrowven DC. Dainty RF. Tetrahedron Lett.  1996,  37:  7659 
    Google Scholar
  • 2g Fujimoto K. Tokuda Y. Maekawa H. Matsubara Y. Mizuno T. Nishiguchi I. Tetrahedron  1996,  52:  3889 
    Google Scholar
  • 2h Rogers JF. Green DM. Tetrahedron Lett.  2002,  43:  3585 
    Google Scholar
  • 3a Fyfe CA. In The Chemistry of the Hydroxyl Group   Vol. 1:  Patai S. Wiley-Interscience; New York: 1971.  p.83-124  
    Google Scholar
  • 3b Whiting DA. In Comprehensive Organic Chemistry. The Synthesis and Reactions of Organic Compounds   Vol. 1:  Barton D. Ollis WD. Pergamon; Oxford: 1979.  p.717-730  
    Google Scholar
  • 3c George T. Mabon R. Sweeney G. Sweeney JB. Tavassoli A. J. Chem. Soc., Perkin Trans. 1  2000,  2529 
    Google Scholar
  • 4a Maleczka RE. Shi F. Holmes D. Smith MR. J. Am. Chem. Soc.  2003,  125:  7792 
    Google Scholar
  • 4b Lee Y. Kelly MJ. Tetrahedron Lett.  2006,  47:  4897 
    Google Scholar
  • 5a Anderson KW. Ikawa T. Tundel RE. Buchwald SL. J. Am. Chem. Soc.  2006,  128:  10694 
    Google Scholar
  • 5b Chen G. Chan ASC. Kwong FY. Tetrahedron Lett.  2007,  48:  473 
    Google Scholar
  • 5c Schulz T. Torborg C. Schäffner B. Huang J. Zapf A. Kadyrov R. Börner A. Beller M. Angew. Chem. Int. Ed.  2009,  48:  918 
    Google Scholar
  • 5d Sergeev AG. Schulz T. Torborg C. Spannenberg A. Neumann H. Beller M. Angew. Chem. Int. Ed.  2009,  48:  7595 
    Google Scholar
  • 5e Willis MC. Angew. Chem. Int. Ed.  2007,  46:  3402 
    Google Scholar
  • 6 Gallon BJ. Kojima RW. Kaner RB. Diaconescu PL. Angew. Chem. Int. Ed.  2007,  46:  7251 
    CrossrefGoogle Scholar
  • 7a Kormos CM. Leadbeater NE. Tetrahedron  2006,  62:  4728 
    Google Scholar
  • 7b Zhao D. Wu N. Zhang S. Xi P. Su X. Lan J. You J. Angew. Chem. Int. Ed.  2009,  48:  8729 
    Google Scholar
  • 7c Taillefer M, Monnier F, Tilli A, and Xia N. inventors; FR  02767. 
  • 7d Tlili A. Xia N. Monner F. Taillefer M. Angew. Chem. Int. Ed.  2009,  48:  8725 
    Google Scholar
  • 7e Yang D. Fu H. Chem. Eur. J.  2010,  16:  2366 
    Google Scholar
  • 7f Maurer S. Liu W. Zhang X. Jiang Y. Ma D. Synlett  2010,  976 
    Google Scholar
  • 7g Jing L. Wei J. Zhou L. Huang Z. Li Z. Zhou X. Chem. Commun.  2010,  46:  4767 
    Google Scholar
  • 8 Sheldon RA. Pure Appl. Chem.  2000,  72:  1233 
    CrossrefGoogle Scholar
  • For some recent reviews of copper-catalyzed reactions, see:
  • 9a Monnier F. Taillefer M. Angew. Chem. Int. Ed.  2009,  48:  6954 
    Google Scholar
  • 9b Monnier F. Taillefer M. Angew. Chem. Int. Ed.  2008,  47:  3096 
    Google Scholar
  • 9c Evano G. Blanchard N. Toumi M. Chem. Rev.  2008,  108:  3054 
    Google Scholar
  • 9d Beletskaya IP. Cheprakov AV. Coord. Chem. Rev.  2004,  248:  2337 
    Google Scholar
  • For some recent studies, see:
  • 10a Ramana T. Saha P. Das M. Punniyamurthy T. Org. Lett.  2010,  12:  84 
    Google Scholar
  • 10b Ali MA. Saha P. Punniyamurthy T. Synthesis  2010,  908 
    Google Scholar
  • 10c Jammi S. Krishnamoorthy S. Saha P. Kundu DS. Sakthivel S. Ali MA. Paul R. Punniyamurthy T. Synlett  2009,  3323 
    Google Scholar
  • 10d Saha P. Ramana T. Purkait N. Ali MA. Paul R. Punniyamurthy T. J. Org. Chem.  2009,  74:  8719 
    Google Scholar
  • 10e Jammi S. Sakthivel S. Rout L. Mukherjee T. Mandal S. Mitra R. Saha P. Punniyamurthy T. J. Org. Chem.  2009,  74:  1971 
    Google Scholar
  • For some examples on the use of n-Bu4NOH˙5H2O, see:
  • 11a Guo K. Thompson MJ. Chen B. J. Org. Chem.  2009,  74:  6999 
    Google Scholar
  • 11b Mori A. Shimada T. Kondo T. Sekiguchi A. Synlett  2001,  649 
    Google Scholar
  • 11c Mori A. Kawashira J. Shimada T. Suguro M. Hirabayashi K. Nishihara Y. Org. Lett.  2000,  2:  2935 
    Google Scholar
  • For recent studies using 8-hydroxyquinalidine, see:
  • 12a Taubmann S. Alt HG. J. Mol. Catal. A: Chem.  2008,  289:  44 
    Google Scholar
  • 12b Taubmann S. Alt HG. J. Mol. Catal. A: Chem.  2008,  289:  49 
    Google Scholar
  • For some recent examples on the use of 8-hydroxyquinoline for cross-coupling reactions, see:
  • 13a Liu L. Frohn M. Xi N. Dominguez C. Hungate R. Reider PJ. J. Org. Chem.  2005,  70:  10135 
    Google Scholar
  • 13b Niu J. Guo P. Kang J. Li Z. Xu J. Hu S. J. Org. Chem.  2009,  74:  5075 
    Google Scholar
  • 14 Wang YF. Deng W. Liu L. Guo QX. Chin. Chem. Lett.  2005,  16:  1197 
    Google Scholar
  • 15 Dahlenburg L. Treffert H. Farr C. Heinemann FW. Zahl A. Eur. J. Inorg. Chem.  2007,  1738 
    CrossrefGoogle Scholar
  • 16 Kwong FY. Buchwald SL. Org. Lett.  2002,  4:  3517 
    CrossrefPubMedGoogle Scholar
  • 17a Xia N. Taillefer M. Chem. Eur. J.  2008,  14:  6037 
    Google Scholar
  • 17b Bistri O. Correa A. Bolm C. Angew. Chem. Int. Ed.  2008,  47:  586 
    Google Scholar
  • 18a Goossen LJ. Rodriguez N. Lange PP. Linder C. Angew. Chem. Int. Ed.  2010,  49:  1111 
    Google Scholar
  • 18b Gujadhur R. Bates CG. Venkataraman D. Org. Lett.  2001,  3:  4315 
    Google Scholar
  • 18c Mansour M. Giacovazzi R. Ouali A. Taillefer M. Jutand A. Chem. Commun.  2008,  6051 
    Google Scholar
  • 19 Monnier F. Turtaut F. Duroure L. Taillefer M. Org. Lett.  2008,  10:  3203 
    CrossrefPubMedGoogle Scholar
  • 20a Powell DA. Maki T. Fu GC. J. Am. Chem. Soc.  2005,  127:  510 
    Google Scholar
  • 20b Bercot EA. Rovis T. J. Am. Chem. Soc.  2005,  127:  247 
    Google Scholar
  • 20c Yi X.-Y. Chan K.-W. Huang EK. Sau Y.-K. Williams ID. Leung W.-H. Eur. J. Inorg. Chem.  2010,  2369 
    Google Scholar
  • 21a Zhu W. Ma D. Chem. Commun.  2004,  888 
    Google Scholar
  • 21b Ki J. Chang S. Chem. Commun.  2008,  3052 
    Google Scholar
  • 21c Ma D. Geng Q. Zhang H. Jiang Y. Angew. Chem. Int. Ed.  2010,  49:  1291 
    Google Scholar
  • 22 Furniss BS. Hannaford AJ. Smith PWG. Tatchell AR. Vogel’s Textbook of Practical Organic Chemistry   5th ed.:  Pearson Education; Singapore: 2004.  p.930-931  
    Google Scholar