Nanocrystalline magnesium oxide stabilized gold nanoparticles: An advanced nanotechnology based recyclable heterogeneous catalyst platform for the one-pot synthesis of propargylamines

Green Chemistry

Volumn 13, Issue 10, 2011, Pages 2878-2887

  Layek, Keya ^a   Chakravarti, Rajashree ^b   Lakshmi Kantam, M ^a   Maheswaran, H ^a   Vinu, Ajayan ^b  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

^b NATIONAL INSTITUTE FOR MATERIALS SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 80053551941     PISSN: 14639262     EISSN: 14639270     Source Type: Journal    
DOI: 10.1039/c1gc15518k     Document Type: Article

References (74)

1. O. Vaughan Nat. Nanotechnol. 2010 5 5.
2. B. Hammer J. K. Norskov Nature 1995 376 238.
3. G. J. Hutchings M. Brust H. Schmidbaur Chem. Soc. Rev. 2008 37 1759.
4. A. S. K. Hashmi L. Schwarz J.-H. Choi T. M. Frost Angew. Chem., Int. Ed. 2000 39 2285.
5. A. S. K. Hashmi T. M. Frost J. W. Bats J. Am. Chem. Soc. 2000 122 11553.
6. N. Asao K. Takahashi S. Lee T. Kasahara Y. Yamamoto J. Am. Chem. Soc. 2002 124 12650.
7. G. R. Brown A. M. Bamford J. Bowyer D. S. James N. Rankine E. Tang V. Torr E. J. Culbert Bioorg. Med. Chem. Lett. 2000 10 575.
8. A. D. Melhado W. E Brenzovich A. D. Lackner F. D. Troste J. Am. Chem. Soc. 2010 132 8885.
9. C. Wei C.-J. Li J. Am. Chem. Soc. 2003 125 9584.
10. B. Huang X. Yao C.-J. Li Adv. Synth. Catal. 2006 348 1528.
11. Y. Yan Y. Liu Org. Lett. 2007 9 4323 Also see reference 11 for the one-pot synthesis of propargylamines catalyzed by recyclable cationic gold complexes.
12. B. Ringdahl, in The Muscarinic Receptors, ed. J. H. Brown, Humana Press, Clifton NJ, 1989.
13. M. Miura M. Enna K. Okuro M. Nomura J. Org. Chem. 1995 60 4999.
14. A. Jenmalm W. Berts Y. L. Li K. Luthman I. Csoregh U. Hacksell J. Org. Chem. 1994 59 1139.
15. G. Dyker Angew. Chem. 1999 111 1808.
16. Angew. Chem., Int. Ed. 1999 38 1698.
17. M. Yogev-Falach T. Amit B.-O. Am M. B. H. Youdim Faseb J. 2003 17 2325.
18. C. Binda F. Hubalek M. Li Y. Herzig J. Sterling D. E. Edmondson A. Mattevi J. Med. Chem. 2004 47 1767.
19. Also visit the website http://en.wikipedia.org/wiki/Rasagiline for additional details on rasagiline.
20. D. A. Gallagher A. Schrag CNS Drugs 2008 22 563.
21. For synthesis of propargylamines using other than gold based catalysts: see: W.-W. Chen R. Nguyen C.-J. Li Tetrahedron Lett. 2009 50 2895.
22. G. Ren J. Zhang Z. Duan M. Cui Y. Wu Aust. J. Chem. 2009 62 75.
23. S. B. Park H. Alper Chem. Commun. 2005 1315.
24. M. K. Patil M. Keller B. M. Reddy P. Pale J. Sommer Eur. J. Org. Chem. 2008 4440.
25. P. Lia L. Wang Tetrahedron 2007 63 5455.
26. M. L. Kantam S. Laha J. Yadav S. Bhargava Tetrahedron Lett. 2008 49 3083.
27. M. L. Kantam V. Balasubrahmanyam K. B. Shiva Kumar G. T. Venkanna Tetrahedron Lett. 2007 48 7332.
28. A. S. K. Hashmi Gold Bull. 2003 36 3.
29. G. Dyker Angew. Chem., Int. Ed. 2000 39 4237.
30. A. Hoffmann-Röder N. Krause Org. Biomol. Chem. 2005 3 387.
31. X. Zhang A. Corma Chem. Commun. 2007 3080.
32. A. Corma Catal. Rev. 2004 46 369.
33. R. A. Widenhoefer X. Han Eur. J. Org. Chem. 2006 4555.
34. J. H. Teles S. Brode M. Chabanas Angew. Chem. 1998 110 1475.
35. Angew. Chem., Int. Ed. 1998 37 1415.
36. Y. Fukuda K. Utimoto J. Org. Chem. 1991 56 3729.
37. X. Zhang A. Corma Dalton Trans. 2008 397.
38. Y. Fukuda K. Utimoto H. Nozaki Heterocycles 1987 25 297.
39. Y. Fukuda K. Utimoto Synthesis 1991 975.
40. T. E. Müller Tetrahedron Lett. 1998 39 5961.
41. For synthesis of propargylamines catalyzed by recyclable cationic gold complexes see: V. K-Y. Lo K.-Y. Kung M.-K. Wong C.-M. Che J. Organomet. Chem. 2009 694 583.
42. B. T. Elie C. Levine I. U. Belandio A. V. Ramirez R. J. Aguilera R. Ovalle M. Contel Eur. J. Inorg. Chem. 2009 3421.
43. X. Zhang A. Corma Angew. Chem., Int. Ed. 2008 47 4358.
44. V. K-Y. Lo Y. Liu M.-K. Wong C.-M. Che Org. Lett. 2006 8 1529.
45. M. L. Kantam B. V. Prakash C. R. V. Reddy B. Sreedhar Synlett 2005 15 2329.
46. M. Kidwai V. Bansal A. Kumar S. Mozumdar Green Chem. 2007 9 742.
47. K. K. R. Datta B. V. S. Reddy K. Ariga A. Vinu Angew. Chem., Int. Ed. 2010 49 5961.
48. P. Jeevanandam K. J. Klabunde Langmuir 2002 18 5309.
49. K. J. Klabunde, and R. Mulukutla, Nanoscale Materials in Chemistry, Wiley Interscience, New York, 2001, Chapter 7, p 223.
50. Please visit the website http://www.nanoscalecorp.com/ for complete characterization data of NAP-MgO.
51. B. M. Choudary K. Jyothi M. Roy M. L. Kantam B. Sreedhar Adv. Synth. Catal. 2004 346 1471.
52. M. L. Kantam U. Pal B. Sreedhar S. Bhargava I. Iwasawa M. Tada B. M. Choudary Adv. Synth. Catal. 2008 350 1225.
53. M. L. Kantam J. Yadav S. Laha B. Sreedhar S. Bhargava Adv. Synth. Catal. 2008 350 2575.
54. M. L. Kantam S. Roy M. Roy M. S. Subhas P. R. Likhar B. Sreedhar B. M. Choudary Synlett 2006 17 2747.
55. K. Layek H. Maheswaran M. L. Kantam R. Arundhathi S. Bhargava Adv. Synth. Catal. 2011 353 606.
56. M. L. Kantam R. Chakravarti U. Pal B. Sreedhar S. Bhargava Adv. Synth. Catal. 2008 350 822.
57. M. L. Kantam R. Chakravarti V. R. Chintareddy B. Sreedhar S. Bhargava Adv. Synth. Catal. 2008 350 2544.
58. K. Zhu J. Hu C. Kubel R. Richards Angew. Chem., Int. Ed. 2006 45 7277.
59. A. L. Patterson Phys. Rev. 1939 56 978.
60. For an elaborate discussion on XRD patterns of Au(0) nanoparticles, hydrated hexagonal crystalline phase of magnesium oxide and cubic crystalline phase of magnesium oxide, respectively see: F. Zhao Y. Yang Colloid J. 2010 72 346.
61. Y. Ding G. Zhang H. Wu B. Hai L. Wang Y. Qian Chem. Mater. 2001 13 435.
62. M. B. M. Reddy S. Ashoka G. T. Chandrappa M. A. Pasha Catal. Lett. 2010 138 82.
63. W. Z. Steurer Kristallogr. 2004 21 9391.
64. D. Shechtman I. Blech D. Gratias J. Cahn Phys. Rev. Lett. 1984 53 1951.
65. A. Quivy M. Quiquandon Y. Calvayrac F. Faudot D. Gratias C. Berger R. A. Brand V. Simonetk F. Hippertk J. Phys.: Condens. Matter 1996 8 4223.
66. J.-N. Barbier N. Tamura J.-L. Verger-Gaugry J. Non-Cryst. Solids 1993 153–154 126.
67. S. Samai G. C. Nandi M. S. Singh Tetrahedron Lett. 2010 51 5555.
68. L. Zani T. Eichhorn C. Bolm Chem.–Eur. J. 2007 13 2587.
69. J. S. Yadav B. V. S. Reddy A. V. Hara Gopal K. S. Patil Tetrahedron Lett. 2009 50 3493.
70. B. Sreedhar A. S. Kumar P. S. Reddy Tetrahedron Lett. 2010 51 1891.
71. E. Ramu R. Varala N. Sreelatha S. R. Adapa Tetrahedron Lett. 2007 48 7184 Also see references 8b, 8f and 13.
72. J. March, Advanced Organic Chemistry, 4th ed., 1992, Wiley, New York.
73. X. Zhang A. Corma Angew. Chem., Int. Ed. 2008 47 4358 Also see references 8f and 8g.
74. S. Zhang K. L. Chandra C. B. Gorman J. Am. Chem. Soc. 2006 129 4876.