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Catalytic performance study of nano-cobalt: a catalyst for complement to the Heck coupling reaction

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Abstract

Easy and convenient synthesis of crystalline cobalt-nanoparticles by a seed mediated growth method with cetyltrimethylammonium bromide used as surfactant, KI as an additive and ascorbic acid as reductant; this synthesized Co-nanoparticle are characterized by XRD and TEM analysis, and is used as a coupling catalyst for alkenes with aryl halides in the presence of a base. The yield of the catalyzed product and the method has many advantages such as affordable and ligand-free condition. Hence overall reaction is augmented to the Heck coupling reaction.

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References

  1. V. Polshettiwar, R. Luque, A. Fihri, H. Zhu, M. Bouhrara, J.M. Basset, Chem. Rev. 111, 3036 (2011)

    Article  CAS  Google Scholar 

  2. K. Esumi, K. Tano, K. Meguro, Chem. Mater. 2, 564 (1990)

    Article  CAS  Google Scholar 

  3. J.S. Bradley, E.W. Hill, B. Chudret, A. Duteil, Chem. Mater. 5, 254 (1993)

    Article  CAS  Google Scholar 

  4. N.R. Jana, Z.L. Wang, T. Pal, Langmuir 16, 2457 (2000)

    Article  CAS  Google Scholar 

  5. A. Henglein, J. Phys. Chem. B 97, 5457 (1993)

    Article  CAS  Google Scholar 

  6. Y. Yonezawa, T. Sato, M. Ohno, H. Hada, J. Chem. Soc. Faraday Trans. 1 83, 1559 (1987)

    Article  CAS  Google Scholar 

  7. K. Torigoe, K. Esumi, Langmuir 8, 59 (1992)

    Article  CAS  Google Scholar 

  8. H. Hirai, Y. Nakamura, N. Toshima, J. Macromol, Sci. Part A 13, 727 (1979)

    CAS  Google Scholar 

  9. K. Torigoe, Y. Nakajima, K. Esumi, J. Phys. Chem. 97, 8304 (1993)

    Article  CAS  Google Scholar 

  10. S.O. Obare, N.R. Jana, C.J. Murphy, Nano Lett. 1, 601 (2001)

    Article  CAS  Google Scholar 

  11. T.K. Sau, C.J. Murphy, Langmuir 21, 2923 (2005)

    Article  CAS  Google Scholar 

  12. B. Nikoobakht, M.A. El-Sayed, Langmuir 17, 6368 (2001)

    Article  CAS  Google Scholar 

  13. X. Ye, L. Jin, H. Caglayan, J. Chen, G. Xing, C. Zheng, V. Doan-Nguyen, Y. Kang, N. Engheta, C.R. Kagan, C.B. Murray, ACS Nano 6, 2804 (2012)

    Article  CAS  Google Scholar 

  14. H.Y. Wu, W.L. Huang, M.H. Huang, Cryst. Growth Des. 7, 831 (2007)

    Article  CAS  Google Scholar 

  15. X. Ma, J. Feng, F. You, J. Ma, X. Zhou, M. C. Wang, Chin. Phys. B 23, 087807 (2014)

    Article  Google Scholar 

  16. T. Mizoroki, K. Mori, A. Ozaki, Bull. Chem. Soc. Jpn. 44, 581 (1971)

    Article  CAS  Google Scholar 

  17. R.F. Heck, J.P. Nolley, J. Org. Chem. 37, 2320 (1972)

    Article  CAS  Google Scholar 

  18. A. de Meijere, F. Diederich, Metal-Catalyzed Cross-Coupling Reactions, 2nd edn, Chap. 3. (Wiley-VCH Verlag GmbH, Weinheim, 2004)

    Book  Google Scholar 

  19. F. Diederich, P.J. Stang (eds.), Metal-Catalyzed Cross-Coupling Reactions, Chap. 3. (Wiley-VCH, Weinheim, 1998)

    Google Scholar 

  20. J.T. Link, L.E. Overman, in Metal-Catalyzed Cross-Coupling Reactions (Wiley-VCH, Weinheim, 2007), p. 230

    Book  Google Scholar 

  21. F. Diederich, P.J. Stang, (eds.), Metal-Catalyzed Cross-Coupling Reactions, Chap. 6. (Wiley-VCH, Weinheim, 1998)

    Google Scholar 

  22. C. Amatore, E. Carre, A. Jutand, Organometallics 14, 5605 (1995)

    Article  CAS  Google Scholar 

  23. A. de Meijere, F. Diederich, (eds.), Metal-Catalyzed Cross-Coupling Reactions, Chap. 5. (Wiley-VCH, Weinheim, 2004)

    Google Scholar 

  24. R.F. Heck Org. React. 27, 345 (1982)

    CAS  Google Scholar 

  25. I.P. Beletskaya, A.V. Cheprakov, Chem. Rev. 100, 3009 (2000)

    Article  CAS  Google Scholar 

  26. G.T. Crips, Chem. Soc. Rev. 27, 427 (1998)

    Article  Google Scholar 

  27. A. de Meijere, F.E. Meyer, Angew. Chem. Int. Ed. Engl. 33, 2379 (1994)

    Article  Google Scholar 

  28. W. Cabri, I. Candiani, Acc. Chem. Res. 28, 2 (1995)

    Article  CAS  Google Scholar 

  29. J.M. Gaudin, Tetrahedron Lett. 32, 6113 (1991)

    Article  CAS  Google Scholar 

  30. L.E. Overman, D.J. Ricca, V.D. Tran, J. Am. Chem. Soc. 115, 2042 (1993)

    Article  CAS  Google Scholar 

  31. L.F. Tietze, W. Buhr, Angew. Chem. Int. Ed. Engl. 34, 1366 (1995)

    Article  CAS  Google Scholar 

  32. R.R. Bader, P. Baumeister, U. H. Blaser, Chimia (Aarau) 50, 99 (1996)

    CAS  Google Scholar 

  33. T.C. Wu, US Patent 5536870, (1996)

  34. A. Eisenstadt, in Catalysis of Organic Reactions, ed. by F.E. Herkes (Marcel Dekker, New York, 1998)

    Google Scholar 

  35. T. Mino, Y. Shirae, Y. Sasai, M. Sakamoto, T. Fujita, J. Org. Chem. 71, 6834 (2006)

    Article  CAS  Google Scholar 

  36. G. Zou, W. Huang, W.J. Xiao, J. Tang, New J. Chem. 30, 803 (2006)

    Article  CAS  Google Scholar 

  37. J. Dupont, M. Pfeffer, J. Spencer, Eur. J. Inorg. Chem. 2001, 1917 (2001)

    Article  Google Scholar 

  38. R.B. Bedford, Chem. Commun. 2003, 1787 (2003)

    Article  Google Scholar 

  39. W.A. Herrmann, Angew. Chem. Int. Ed. 41, 1290 (2002)

    Article  CAS  Google Scholar 

  40. R.B. Bedford, C.S.J. Cazin, D. Holder, Coord. Chem. Rev. 248, 2283 (2004)

    Article  CAS  Google Scholar 

  41. D.J. Nielsen, K.J. Cavell, B.W. Skelton, A.H. White, Inorg. Chim. Acta 359, 1855 (2006)

    Article  CAS  Google Scholar 

  42. C. Tubaro, A. Biffis, C. Gonzato, M. Zecca, M. Basato, J. Mol. Catal. A 248, 93 (2006)

    Article  CAS  Google Scholar 

  43. R. Wang, B. Twamley, J.M. Shreeve, J. Org. Chem. 71, 426 (2006)

    Article  CAS  Google Scholar 

  44. J. Masllorens, M. Moreno-Manas, A. Pla-Quintana, A. Roglans, Org. Lett. 5, 1559 (2003)

    Article  CAS  Google Scholar 

  45. T.M. Gall, A. Birkner, G. Dyker, Organomet. Chem. 693(1), 1 (2008)

    Article  Google Scholar 

  46. R. Narayanan, M.A. El-Sayed, J. Am. Chem. Soc. 125(27), 8340 (2003)

    Article  CAS  Google Scholar 

  47. A.M. Doyle, S.K. Shaikhutdinov, S.D. Jackson, H.J. Freund, Angew. Chem. Int. Ed. 42, 5240 (2003)

    Article  CAS  Google Scholar 

  48. M. Singla, P. Mathur, M. Gupta, M.S. Hundal, Trans. Met. Chem. 33, 175 (2008)

    Article  CAS  Google Scholar 

  49. A.F. Littke, G.C. Fu, J. Org. Chem. 64, 10 (1999)

    Article  CAS  Google Scholar 

  50. K. Selvakumar, A. Zapf, M. Beller, Org. Lett. 4, 3031 (2002)

    Article  CAS  Google Scholar 

  51. D. Gelman, S.L. Buchwald, Angew. Chem. Int. Ed. 42, 5993 (2003)

    Article  CAS  Google Scholar 

  52. W. Affo, H. Ohmiya, T. Fujioka, Y. Ikeda, T. Nakamura, H. Yorimitsu, K. Oshima, Y. Imamura, T. Mizuta, K. Miyosh, J. Am. Chem. Soc. 128, 8068 (2006)

    Article  CAS  Google Scholar 

  53. Y. Ikeda, T. Nakamura, H. Yorimitsu, K. Oshima, J. Am. Chem. Soc. 124, 6514 (2002)

    Article  CAS  Google Scholar 

  54. P. Gomes, C. Gosmini, J.Y. Nedelec, J. Perichon, Tetrahedron Lett. 43, 5901 (2002)

    Article  CAS  Google Scholar 

  55. P. Gomes, C. Gosmini, J. Perichon, Tetrahedron 59, 2999 (2003)

    Article  CAS  Google Scholar 

  56. Y.G. Li, P. Zhou, Z.H. Dai, Z.X. Hu, P.P. Sun, J.C. Bao, New J. Chem. 30, 832 (2006)

    Article  CAS  Google Scholar 

  57. P. Zhou, Y. Li, P. Sun, J. Zhou, J. Bao, Chem. Commun. 2007, 1418 (2007)

    Article  Google Scholar 

  58. W. Affo, H. Ohmiya, T. Fujioka, Y. Ikeda, T. Nakamura, H. Yorimitsu, K. Oshima, Y. Imamura, T. Mizuta, K. Miyoshi, J. Am. Chem. Soc. 128, 8068 (2006)

    Article  CAS  Google Scholar 

  59. K.S. Jithendra kumara, G. Krishnamurthy, B.E. Kumara swamy, N.D. Shashi kumar, Satish naika, B.S. Krishna, Nagaraj naik. Appl. Organometal. Chem. 31(1), 3549 (2017). doi:10.1002/aoc.3549

    Google Scholar 

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Funding

The funding was provided by University Grants Commission (Grant No. UGC:MRP(S)-0098/12-13/KAKU023/UGC-SWRO/dated:01-10-2013).

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Correspondence to G. Krishnamurthy.

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Jithendra Kumara, K.S., Krishnamurthy, G., Kumara Swamy, B.E. et al. Catalytic performance study of nano-cobalt: a catalyst for complement to the Heck coupling reaction. J Porous Mater 24, 1095–1103 (2017). https://doi.org/10.1007/s10934-016-0350-5

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