Synlett 2009(16): 2663-2668  
DOI: 10.1055/s-0029-1217958
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Facile CuI-Catalyzed Arylation of Azoles and Amides Using Simple Enaminones as Efficient Ligands

Cungui Chenga, Gonglei Suna, Jieping Wanb, Cuirong Sun*b
a Department of Chemistry, Zhejiang Normal University, Jinhua 321004, P. R. of China
b Department of Chemistry, Zhejiang University, Hangzhou 310027, P. R. of China
Fax: +86(571)87951629; e-Mail: suncuirong@zju.edu.cn;
Further Information

Publication History

Received 16 June 2009
Publication Date:
04 September 2009 (online)

Abstract

(E)-3-(Dimethylamino)-1-(2-hydroxyphenyl)prop-2-en-1-one was found to be an excellent ligand for copper-catalyzed N-arylation of azoles and amides with aryl halides under mild conditions. The reaction took place at 82 ˚C in MeCN with broad functional-group compatibility. A combination of the ligand and CuI proved to be an efficient catalytic system to promote the coupling reactions of aryl halides with azoles and amides.

    References and Notes

  • 1 Ullmann F. Ber. Dtsch. Chem. Ges.  1903,  36:  2382 
  • 2 Goldberg I. Ber. Dtsch. Chem. Ges.  1906,  39:  1691 
  • 3a Guram AS. Buchwald SL. J. Am. Chem. Soc.  1994,  116:  7901 
  • 3b Peat AJ. Buchwald SL. J. Am. Chem. Soc.  1996,  118:  1028 
  • 3c Wolfe JP. Wagaw S. Buchwald SL. Acc. Chem. Res.  1998,  31:  805 
  • 3d Wolfe JP. Buchwald SL. J. Org. Chem.  2000,  65:  1144 
  • 3e Klapars A. Huang X. Buchwald SL. J. Am. Chem. Soc.  2002,  124:  7421 
  • 3f Strieter ER. Buchwald SL. J. Am. Chem. Soc.  2005,  127:  4120 
  • 3g Anderson KW. Tundel RE. Ikawa T. Altman RA. Buchwald SL. Angew. Chem. Int. Ed.  2006,  45:  6523 
  • 3h Biscoe MR. Barder TE. Buchwald SL. Angew. Chem. Int. Ed.  2007,  46:  7232 
  • 4a Paul F. Patt J. Hartwig JF. J. Am. Chem. Soc.  1994,  116:  5969 
  • 4b Hartwig JF. Richards S. Baranano D. Paul F. J. Am. Chem. Soc.  1996,  118:  3626 
  • 4c Hartwig JF. Synlett  1997,  329 
  • 4d Shaughnessy KH. Hamann BC. Hartwig JF. J. Org. Chem.  1998,  63:  6546 
  • 4e Stauffer SR. Lee S. Stambuli JP. Hauck SI. Hartwig JF. Org. Lett.  2002,  2:  1423 
  • 4f Stambuli JP. Kuwano R. Hartwig JF. Angew. Chem. Int. Ed.  2002,  41:  4746 
  • 5a Guram AS. King AO. Allen JG. Wang X. Schenkel LB. Chan J. Bunel EE. Faul MM. Larsen RD. Martinelli MJ. Reider PJ. Org. Lett.  2006,  8:  1787 
  • 5b Fei Z. Zhao D. Pieraccini D. Ang WH. Geldbach TJ. Scopelliti R. Chiappe C. Dyson PJ. Organometallics  2007,  26:  1588 
  • 5c Handy ST. Sabatini JJ. Org. Lett.  2006,  8:  1537 
  • 5d Hassan J. Sevignon M. Gozzi C. Schulz E. Lemaire M. Chem. Rev.  2002,  102:  1359 
  • 6a Kondo T. Mitsudo T. Chem. Rev.  2000,  100:  3205 
  • 6b Strieter ER. Blackmond DG. Buchwald SL. J. Am. Chem. Soc.  2003,  125:  13978 
  • 6c Lewis AK. Caddick S. Cloke FGN. Billingham NC. Hitchcock PB. Leonard J. J. Am. Chem. Soc.  2003,  125:  10066 
  • 6d Vorogushin AV. Huang X. Buchwald SL. J. Am. Chem. Soc.  2005,  127:  8146 
  • 7 Thomas AW. Ley SV. Angew. Chem. Int. Ed.  2003,  42:  5400 
  • 8a Kiyomori A. Marcoux JF. Buchwald SL. Tetrahedron Lett.  1999,  40:  2657 
  • 8b Kwong FY. Buchwald SL. Org. Lett.  2003,  5:  793 
  • 8c Antilla JC. Baskin JM. Barder TE. Buchwald SL. J. Org. Chem.  2004,  69:  5578 
  • 8d Martin R. Rivero MR. Buchwald SL. Angew. Chem. Int. Ed.  2006,  45:  7079 
  • 8e Altman RA. Buchwald SL. Org. Lett.  2006,  8:  2779 
  • 8f Jones CP. Anderson KW. Buchwald SL. J. Org. Chem.  2007,  72:  7968 
  • 8g Altman RA. Buchwald SL. Org. Lett.  2007,  9:  643 
  • 8h Shafir A. Buchwald SL. J. Am. Chem. Soc.  2006,  128:  8742 
  • 8i Kwong FY. Klapars A. Buchwald SL. Org. Lett.  2002,  4:  581 
  • 9a Ma D. Jiang J. Tetrahedron: Asymmetry  1998,  9:  1137 
  • 9b Ma D. Zhang Y. Yao J. Wu S. Tao F. J. Am. Chem. Soc.  1998,  120:  12459 
  • 9c Ma D. Xia C. Org. Lett.  2001,  3:  2583 
  • 9d Ma D. Xia C. Jiang J. Zhang J. Tang W.
    J. Org. Chem.  2003,  68:  442 
  • 9e Ma D. Cai Q. Synlett  2004,  128 
  • 9f Zou B. Yuan Q. Ma D. Angew. Chem. Int. Ed.  2007,  46:  2598 
  • 9g He G. Wang J. Ma D. Org. Lett.  2007,  9:  1367 
  • 10a Ma D. Cai Q. Zhang H. Org. Lett.  2003,  5:  2453 
  • 10b Cai Q. Zhu W. Zhang H. Zhang Y. Ma D. Synthesis  2005,  496 
  • 10c Zhang H. Cai Q. Ma D. J. Org. Chem.  2005,  70:  5164 
  • 10d Evano G. Blanchard N. Toumi M. Chem. Rev.  2008,  108:  3054 
  • 10e Jerphagnon T. Van Klink GPM. De Vries JG. Van Koten G. Org. Lett.  2005,  7:  5241 
  • 10f Yip SF. Cheung HY. Zhou Z. Kwong FY. Org. Lett.  2007,  9:  3469 
  • 10g Klapars A. Antilla JC. Huang X. Buchwald SL. J. Am. Chem. Soc.  2001,  123:  7727 
  • 11a Xu L. Zhu D. Wu F. Wang R. Wan B. Tetrahedron  2005,  61:  6553 
  • 11b Zhang Z. Mao J. Zhu D. Wu F. Chen H. Wan B. Tetrahedron  2006,  62:  4435 
  • 12 Zhu R. Xing L. Wang X. Cheng C. Su D. Hu Y. Adv. Synth. Catal.  2008,  350:  1253 
  • 13 Zhu L. Li G. Luo L. Guo P. Lan J. You J. J. Org. Chem.  2009,  74:  2200 
  • 14 Wan J. Chai Y. Wu J. Pan Y. Synlett  2008,  3068 
15

General Procedure
All chemicals were obtained from commercial source and used without further purification. A stirred suspension of aryl halides (0.5 mmol), azoles or amides (0.5 mmol), CuI powder (0.05 mmol), Cs2CO3 (1.0 mmol), and L5 (0.1 mmol) in MeCN was refluxed for 12 h (monitored by TLC) under nitrogen. After the mixture was cooled to r.t., the MeCN was removed in vacuo. The solid was then extracted with EtOAc (3 × 10 mL), washed with H2O (3 × 10 mL), and dried over Na2SO4. After the solvent was removed, the crude mixture was purified by silica gel column chromatography to provide the desired product.