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.
Similar content being viewed by others
References
V. Polshettiwar, R. Luque, A. Fihri, H. Zhu, M. Bouhrara, J.M. Basset, Chem. Rev. 111, 3036 (2011)
K. Esumi, K. Tano, K. Meguro, Chem. Mater. 2, 564 (1990)
J.S. Bradley, E.W. Hill, B. Chudret, A. Duteil, Chem. Mater. 5, 254 (1993)
N.R. Jana, Z.L. Wang, T. Pal, Langmuir 16, 2457 (2000)
A. Henglein, J. Phys. Chem. B 97, 5457 (1993)
Y. Yonezawa, T. Sato, M. Ohno, H. Hada, J. Chem. Soc. Faraday Trans. 1 83, 1559 (1987)
K. Torigoe, K. Esumi, Langmuir 8, 59 (1992)
H. Hirai, Y. Nakamura, N. Toshima, J. Macromol, Sci. Part A 13, 727 (1979)
K. Torigoe, Y. Nakajima, K. Esumi, J. Phys. Chem. 97, 8304 (1993)
S.O. Obare, N.R. Jana, C.J. Murphy, Nano Lett. 1, 601 (2001)
T.K. Sau, C.J. Murphy, Langmuir 21, 2923 (2005)
B. Nikoobakht, M.A. El-Sayed, Langmuir 17, 6368 (2001)
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)
H.Y. Wu, W.L. Huang, M.H. Huang, Cryst. Growth Des. 7, 831 (2007)
X. Ma, J. Feng, F. You, J. Ma, X. Zhou, M. C. Wang, Chin. Phys. B 23, 087807 (2014)
T. Mizoroki, K. Mori, A. Ozaki, Bull. Chem. Soc. Jpn. 44, 581 (1971)
R.F. Heck, J.P. Nolley, J. Org. Chem. 37, 2320 (1972)
A. de Meijere, F. Diederich, Metal-Catalyzed Cross-Coupling Reactions, 2nd edn, Chap. 3. (Wiley-VCH Verlag GmbH, Weinheim, 2004)
F. Diederich, P.J. Stang (eds.), Metal-Catalyzed Cross-Coupling Reactions, Chap. 3. (Wiley-VCH, Weinheim, 1998)
J.T. Link, L.E. Overman, in Metal-Catalyzed Cross-Coupling Reactions (Wiley-VCH, Weinheim, 2007), p. 230
F. Diederich, P.J. Stang, (eds.), Metal-Catalyzed Cross-Coupling Reactions, Chap. 6. (Wiley-VCH, Weinheim, 1998)
C. Amatore, E. Carre, A. Jutand, Organometallics 14, 5605 (1995)
A. de Meijere, F. Diederich, (eds.), Metal-Catalyzed Cross-Coupling Reactions, Chap. 5. (Wiley-VCH, Weinheim, 2004)
R.F. Heck Org. React. 27, 345 (1982)
I.P. Beletskaya, A.V. Cheprakov, Chem. Rev. 100, 3009 (2000)
G.T. Crips, Chem. Soc. Rev. 27, 427 (1998)
A. de Meijere, F.E. Meyer, Angew. Chem. Int. Ed. Engl. 33, 2379 (1994)
W. Cabri, I. Candiani, Acc. Chem. Res. 28, 2 (1995)
J.M. Gaudin, Tetrahedron Lett. 32, 6113 (1991)
L.E. Overman, D.J. Ricca, V.D. Tran, J. Am. Chem. Soc. 115, 2042 (1993)
L.F. Tietze, W. Buhr, Angew. Chem. Int. Ed. Engl. 34, 1366 (1995)
R.R. Bader, P. Baumeister, U. H. Blaser, Chimia (Aarau) 50, 99 (1996)
T.C. Wu, US Patent 5536870, (1996)
A. Eisenstadt, in Catalysis of Organic Reactions, ed. by F.E. Herkes (Marcel Dekker, New York, 1998)
T. Mino, Y. Shirae, Y. Sasai, M. Sakamoto, T. Fujita, J. Org. Chem. 71, 6834 (2006)
G. Zou, W. Huang, W.J. Xiao, J. Tang, New J. Chem. 30, 803 (2006)
J. Dupont, M. Pfeffer, J. Spencer, Eur. J. Inorg. Chem. 2001, 1917 (2001)
R.B. Bedford, Chem. Commun. 2003, 1787 (2003)
W.A. Herrmann, Angew. Chem. Int. Ed. 41, 1290 (2002)
R.B. Bedford, C.S.J. Cazin, D. Holder, Coord. Chem. Rev. 248, 2283 (2004)
D.J. Nielsen, K.J. Cavell, B.W. Skelton, A.H. White, Inorg. Chim. Acta 359, 1855 (2006)
C. Tubaro, A. Biffis, C. Gonzato, M. Zecca, M. Basato, J. Mol. Catal. A 248, 93 (2006)
R. Wang, B. Twamley, J.M. Shreeve, J. Org. Chem. 71, 426 (2006)
J. Masllorens, M. Moreno-Manas, A. Pla-Quintana, A. Roglans, Org. Lett. 5, 1559 (2003)
T.M. Gall, A. Birkner, G. Dyker, Organomet. Chem. 693(1), 1 (2008)
R. Narayanan, M.A. El-Sayed, J. Am. Chem. Soc. 125(27), 8340 (2003)
A.M. Doyle, S.K. Shaikhutdinov, S.D. Jackson, H.J. Freund, Angew. Chem. Int. Ed. 42, 5240 (2003)
M. Singla, P. Mathur, M. Gupta, M.S. Hundal, Trans. Met. Chem. 33, 175 (2008)
A.F. Littke, G.C. Fu, J. Org. Chem. 64, 10 (1999)
K. Selvakumar, A. Zapf, M. Beller, Org. Lett. 4, 3031 (2002)
D. Gelman, S.L. Buchwald, Angew. Chem. Int. Ed. 42, 5993 (2003)
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)
Y. Ikeda, T. Nakamura, H. Yorimitsu, K. Oshima, J. Am. Chem. Soc. 124, 6514 (2002)
P. Gomes, C. Gosmini, J.Y. Nedelec, J. Perichon, Tetrahedron Lett. 43, 5901 (2002)
P. Gomes, C. Gosmini, J. Perichon, Tetrahedron 59, 2999 (2003)
Y.G. Li, P. Zhou, Z.H. Dai, Z.X. Hu, P.P. Sun, J.C. Bao, New J. Chem. 30, 832 (2006)
P. Zhou, Y. Li, P. Sun, J. Zhou, J. Bao, Chem. Commun. 2007, 1418 (2007)
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)
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
Funding
The funding was provided by University Grants Commission (Grant No. UGC:MRP(S)-0098/12-13/KAKU023/UGC-SWRO/dated:01-10-2013).
Author information
Authors and Affiliations
Corresponding author
Electronic supplementary material
Below is the link to the electronic supplementary material.
Rights and permissions
About this article
Cite this article
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
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10934-016-0350-5