Microwave-assisted Sonogashira cross-coupling reaction catalyzed by Pd-MCM-41 under solvent-free conditions

다국어 초록 (Multilingual Abstract)

In this paper microwave-assisted Sonogashira reactions of phenyl acetylene with aryl iodide using palladium modified Pd-MCM-41, Pd-Y, Pd-VSB-5 and Pd-SBA-15 under solvent-free conditions were described. The results of microwave-assisted Sonogashira reaction using Pd-MCM-41 or Pd-Y in aqueous conditions were also discussed. The microwave-assisted reaction of phenyl acetylene with phenyl iodide using Pd-Y or Pd-MCM-41 and DBU as a base under solvent-free conditions resulted in yields of 85% and 93%, respectively. The reaction with Pd-Y or Pd-MCM-41 using DBU in DMF:H2O (4:1) solution reduced yields to 64% and 76%, respectively.

참고문헌 (Reference)

1 A.M. Sajith, 53 : 5206-, 2012

2 P. Soheili, 5 : 4191-, 2003

3 R. Hosseinzadeh, 40 : 282-, 2010

4 C. Sotiriou-Leventis, 38 : 2285-, 2008

5 E. Awuah, 11 : 3210-, 2009

6 M. Erdelyl, 68 : 6431-, 2003

7 M. Erdelyl, 66 : 4165-, 2001

8 S. Bhattacharya, 45 : 8733-, 2004

9 S. Urgaonkar, 69 : 5752-, 2004

10 Y. liang, 71 : 379-, 2006

11 V. Polshettiwar, 253 : 2599-, 2009

12 F. Alonso, 61 : 11771-, 2005

13 F. Alonso, 64 : 3047-, 2008

14 K. Prabakaran, 52 : 2566-, 2011

15 S. Liu, 270 : 1-, 2007

16 V. Polshettiwar, 63 : 6949-, 2007

17 A. Carpita, 50 : 204-, 2009

18 L. Shao, (413–414) : 267-, 2012

19 B. Domenech, 2012

20 P. Rollet, 241 : 39-, 2005

21 R.N. Gedye, 27 : 279-, 1986

22 R.J. Gigure, 27 : 4945-, 1986

23 A. Loupy, 73 : 161-, 2001

24 Y. Chen, 65 : 8908-, 2009

25 L. Djakovitch, 45 : 1367-, 2004

26 H. Huang, 73 : 6037-, 2008

27 G.W. Kabalka, 57 : 8017-, 2001

28 K. Sonogashira, 16 : 4467-, 1975

29 R. Chinchilla, 107 : 874-, 2007

30 M.M. Heravi, 65 : 7761-, 2009

31 J.-C. Lin, 26 : 3771-, 2010

32 K. Tanaka, "Solvent-free Organic Synthesis" Wiely-VCH 2003

33 C.O. Kappe, "Microwave in Organic and Medicina Chemistry" Wiely- VCH 2005

34 A. de Meijere, "Metal-Catalyzed Cross-Coupling Reactions" Wiley-VCH 2004

35 F. Diederich, "Metal-Catalyzed Cross-Coupling Reactions" Wiley-VCH 1998

36 P.T. Anastas, "Green Chemistry: Theory and Practice" Oxford University Press 1998

37 P.T. Anastas, "Green Chemistry: Designing Chemistry for the Environment" American Chemical Society 1996

38 P. Tundo, "Green Chemistry: Challenging Perspectives" Oxford University Press 2000

39 K. Sonogashira, "Comprehensive Organic Synthesis, vol. 3" Pergamon Press 521-, 1999

40 장원길, "An efficient microwave-assisted Suzuki reaction using Pd/MCM-41 and Pd/SBA-15 as catalysts in solvent-free condition" 한국공업화학회 18 (18): 581-585, 2012

41 Wonghil Chang, "A simple and efficient Suzuki reaction catalyzed by palladium-modified nanopore silica under solvent-free conditions" 한국공업화학회 14 (14): 423-428, 2008