Synthesis 2011(1): 91-96  
DOI: 10.1055/s-0030-1258321
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

CuSO4-Mediated Homocoupling of Arylboronic Acids under Ligand- and Base-Free Conditions in Air

Babak Kaboudin*a,b, Terumitsu Harukib, Tsutomu Yokomatsu*b
a Department of Chemistry, Institute for Advanced Studies in Basic Sciences (IASBS), Zanjan 45137-66731, Iran
Fax: +98(241)4214949; e-Mail: kaboudin@iasbs.ac.ir;
b School of Pharmacy, Tokyo University of Pharmacy and Life Sciences, 1432-1 Horonouchi, Hachioji, Tokyo 192-0392, Japan
Fax: +81(42)676 3239; e-Mail: yokomatu@ps.toyaku.ac.jp;
Further Information

Publication History

Received 28 September 2010
Publication Date:
09 November 2010 (eFirst)

Abstract

The homocoupling of arylboronic acids mediated by very inexpensive and air stable copper(II) sulfate in N,N-dimethylformamide affords the corresponding symmetrical biaryls in moderate to good yields. The homocoupling reaction proceeds in air at 50 ˚C in the presence of molecular sieves without any additives such as base and ligand.

    References

  • 1a Croom KF. Keating GM. Cardiovasc AJ. Drugs  2004,  64:  395 
  • 1b Sharpe M. Jarvis B. Goa KL. Drugs  2001,  61:  1501 
  • 1c Bemis GW. Murcko MA. J. Med. Chem.  1996,  39:  2887 
  • 1d Hajduk PJ. Bures M. Praestgaard J. Fesik EW. J. Med. Chem.  2000,  43:  3443 
  • 1e Bringmann G. Menche D. Acc. Chem. Res.  2001,  34:  615 
  • 2a Bringmann G. Günther C. Ochse M. Schupp O. Tasler S. Biaryls in Nature: A Multi-Faceted Class of Stereochemically, Biosynthetically, and Pharmacologically Intriguing Secondary Metabolites   Springer; New York: 2001. 
  • 2b Horton DA. Bourne GT. Smythe ML. Chem. Rev.  2003,  103:  893 
  • 2c Lloyd-Williams P. Giralt E. Chem. Soc. Rev.  2001,  30:  145 
  • 2d Meier H. Angew. Chem. Int. Ed.  2005,  44:  2482 
  • 3a Suzuki A. Cross-Coupling Reaction of Organoboron Compounds with Organic Halides, In Metal-Catalysed Cross-Coupling Reactions   Diederich F. Stang PT. Wiley-VCH; Weinheim: 1998. 
  • 3b Stanforth SP. Tetrahedron  1998,  54:  263 
  • 4a Miyaura N. Suzuki A. Chem. Rev.  1995,  95:  2457 
  • 4b Hassan J. Sévignon M. Gozzi C. Schulz E. Lemaire M. Chem. Rev.  2002,  102:  1359 
  • 4c Suzuki A.
    J. Organomet. Chem.  1999,  576:  147 
  • 5a Kirai N. Yamamoto Y. Eur. J. Org. Chem.  2009,  1864 
  • 5b Mao J. Hua Q. Xie G. Yao Z. Shi D. Eur. J. Org. Chem.  2009,  2262 
  • 5c Yoshida H. Yamaryo Y. Ohshita J. Kunai A. Tetrahedron Lett.  2003,  44:  1541 
  • 5d Wong MS. Zhang XL. Tetrahedron Lett.  2001,  42:  4087 
  • 5e Lei A. Zhang X. Tetrahedron Lett.  2002,  43:  2525 
  • 6a Miyaura N. Suzuki A. Main Group Met. Chem.  1987,  10:  295 
  • 6b Koza DJ. Carita E. Synthesis  2002,  2183 
  • 6c Kabalka GW. Wang L. Tetrahedron Lett.  2002,  43:  3067 
  • 6d Parrish JP. Jung YC. Floyd RJ. Jung KW. Tetrahedron Lett.  2002,  43:  7899 
  • 6e Klingensmith LM. Leadbeater NE. Tetrahedron Lett.  2003,  44:  765 
  • 6f Yamamoto Y. Suzuki R. Hattori K. Nishiyama N. Synlett  2006,  1027 
  • 7a Amatore C. Cammoun C. Jutand A. Eur. J. Org. Chem.  2008,  4567 
  • 7b Mitsudo K. Shiraga T. Tanaka H. Tetrahedron Lett.  2008,  49:  6593 
  • 8a Suzuki A. J. Organomet. Chem.  1999,  576:  147 
  • 8b Smith KA. Campi EM. Jackson WR. Marcuccio S. Naeslund CGM. Deacon GB. Synlett  1997,  131 
  • 9 Demir AS. Reis O. Emrullahoglu M. J. Org. Chem.  2003,  68:  10130 
  • 10 Evans DA. Katz JL. West TR. Tetrahedron Lett.  1998,  39:  2937 
  • 11 Prokopcová H. Kappe CO. Angew. Chem. Int. Ed.  2009,  48:  2276 
  • 12 Zeng M. Du Y. Shao L. Qi C. Zhang X.-M. J. Org. Chem.  2010,  75:  2556 
  • 13 Courtois V. Barhdadi R. Troupel M. Perichon J. Tetrahedron  1997,  53:  11569 
  • 14 Hartmann CE. Nolan SP. Cazin CSJ. Organometallics  2009,  28:  2915 
  • 15 Nising CF. Schmid UK. Nieger M. Braese S. J. Org. Chem.  2004,  69:  6830 
  • 16 Dong D.-J. Li H.-H. Tian S.-K. J. Am. Chem. Soc.  2010,  132:  5018 
  • 17 Ma N. Zhu Z. Wu Y. Tetrahedron  2007,  63:  4625 
  • 18 Qi C. Sun X. Lu C. Yang J. Du Y. Wu H. Zhang X.-M. J. Organomet. Chem.  2009,  694:  2912