Active-Copper-Promoted Expeditious N-Arylations in Aqueous Media under Microwave Irradiation

Abstract

Active-copper-promoted mild and expeditious N-arylations of amines, amides, imides, and β-lactams with aryl halides under microwave irradiation conditions are reported. These reactions can be performed at 85-90 °C in aqueous media as well as under solvent-free conditions to give good yields. However, under solvent-free conditions, lower yields are obtained.

aqueous media - active copper - β-lactams - microwave - N-arylation - solvent-free

References

1 Ullmann F. Ber. Dtsch. Chem. Ges.  1903,  36:  2382 

2 Lindley J. Tetrahedron  1984,  40:  1433 

3 Hassan J. Sevignon M. Gozzi C. Schulz E. Lemairc M. Chem. Rev.  2002,  102:  1359 

4 Hartwig JF. Angew. Chem. Int. Ed.  1998,  37:  2046 

5 Yang BH. Buchwald SL. J. Organomet. Chem.  1999,  576:  125 

6 Muci AR. Buchwald SL. Top. Curr. Chem.  2002,  219:  131 

7 Oida S. Yashida A. Hayashi T. Naikayama E. Sato S. Okhi E. Tetrahedron Lett.  1980,  21:  619 

8 McCombie SW. Ganguly AK. Girijavallabhan VM. Jeffrey PD. Lin S. Pinto P. McPhail AT. Tetrahedron Lett.  1981,  22:  3489 

9 Joyeau R. Dugenet Y. Wakselman M. J. Chem. Soc., Chem. Commun.  1983,  431 

10 Joyeau R. Yadav LDS. Wakselman M. J. Chem. Soc., Perkin Trans. 1  1987,  1899 

11 Yamamoto T. Kurata Y. Chem. Ind. (London)  1981,  737 

12 Yamamoto T. Kurata Y. Can. J. Chem.  1983,  61:  86 

13 Varma RS. Green Chem.  1999,  1:  43 

14 Perreux L. Loupy A. Tetrahedron  2001,  57:  9199 

15 Lidstrom P. Tierney J. Wathey B. Westman J. Tetrahedron  2001,  57:  9225 

16 Kappe CO. Angew. Chem. Int. Ed.  2004,  43:  6250 

17 Strohmeier GA. Kappe CO. J. Comb. Chem.  2002,  4:  154 

18 Alexandre FR. Domon L. Frere S. Testard A. Thiery V. Besson T. Mol. Diversity  2003,  7:  273 

19 Varma RS. J. Heterocycl. Chem.  1999,  36:  1565 

20 Larhed M. Moberg C. Hallberg A. Acc. Chem. Res.  2002,  35:  717 

21 Hayes BL. In Microwave Technology Chemistry at the Speed of Light   CEM Publishing; Mathews NC: 2002.  p.29 

22 Varma RS. In Microwave Technology Chemical Applications: Kirk-Othmer Encyclopedia of Chemical Technology   5th ed.:  John Wiley & Sons; New York: 2004. 

23 Li J. Chan TH. Organic Reaction in Aqueous Media   John Wiley & Sons; New York: 1997. 

24 Grieco AP. Organic Synthesis in Water   Blackie Academic and Professional; London: 1998. 

25 Kobayashi S. Manabe K. Acc. Chem. Res.  2002,  35:  209 

26 Wei W. Keh CCK. Li CJ. Varma RS. Clean Tech. Environ. Policy  2005,  7:  62 

27 Lindstrom UM. Chem. Rev.  2002,  102:  2751 

28 An J. Bagnell L. Cablewski T. Strauss CR. Trainor RW. J. Org. Chem.  1997,  62:  2505 

29 Strauss CR. Aust. J. Chem.  1999,  52:  83 

30 Ju Y. Varma RS. Green Chem.  2004,  6:  219 

31 Dandia A. Arya K. Sati M. Synth. Commun.  2004,  34:  1141 

32 Ju Y. Varma RS. Org. Lett.  2005,  7:  2409 

33 Yadav LDS. Kapoor R. J. Org. Chem.  2004,  69:  8118 

34 Yadav LDS. Singh A. Tetrahedron Lett.  2003,  44:  5667 

35 Yadav LDS. Singh S. Synthesis  2003,  63 

36 Yadav LDS. Yadav S. Rai VK. Tetrahedron  2005,  61:  10013 

37 Gore PH. Hughes GK. J. Chem. Soc.  1959,  1615