Nickel Catalysts (Heterogeneous)
Christopher R. Sarko,
Marcello DiMare,
Miguel Yus, Francisco Alonso,
Christopher R. Sarko
University of California, Santa Barbara, CA, USA
Search for more papers by this authorMarcello DiMare
University of California, Santa Barbara, CA, USA
Search for more papers by this authorChristopher R. Sarko,
Marcello DiMare,
Miguel Yus, Francisco Alonso,
Christopher R. Sarko
University of California, Santa Barbara, CA, USA
Search for more papers by this authorMarcello DiMare
University of California, Santa Barbara, CA, USA
Search for more papers by this authorAbstract
[7440-02-0] Ni (MW 58.71) InChI = 1S/Ni InChIKey = PXHVJJICTQNCMI-UHFFFAOYSA-N
(hydrogenolyses and hydrogenations1)
Physical Data: mp 1453 °C; bp 2730 °C; d 8.908 g cm−3.
Form Supplied in: powder, rod, wire, foil, or pellet; activated nickel is not commercially available and must be prepared prior to use. 75% nickel on graphite is available.
Preparative Methods: activated nickel is prepared mainly by reduction of nickel dichloride with lithium and a catalytic amount of an arene (naphthalene or 4,4′-di-tert-butylbiphenyl) in tetrahydrofuran. Nickel on alumina can be prepared from Ni(NO3)2·6H2O slurried with Alumina and then dried at 120 °C; The catalyst is activated before use by heating at 400 °C for 30 min.2
Handling, Storage, and Precautions: nickel is stable to air, yet care should be taken to avoid moisture when using finely divided nickel catalysts. Nickel is a possible carcinogen. Use in a fume hood.
Bibliography
- 1 Bartok, M. Stereochemistry of Heterogeneous Metal Catalysis; Wiley: New York, 1985.
- 2 Maier, W. F.; Bergmann, K.; Bleicher, W.; Schleyer, P. v. R. Tetrahedron Lett. 1981, 22, 4227.
- 3 Andrade, J. G.; Maier, W. F.; Zapf, L.; Schleyer, P. v. R. Synthesis 1980, 802. (b) Pines, H.; Shamaiengar, M.; Postl, W. S. J. Am. Chem. Soc. 1955, 77, 5099.
- 4
Grubmuller, P.;
Schleyer, P. v. R.;
McKervey, M. A.
Tetrahedron Lett.
1979,
20,
181.
10.1016/S0040-4039(01)85918-9 Google Scholar
- 5 Maier, W. F.; Grubmuller, P.; Thies, I.; Stein, P. M.; McKervey, M. A.; Schleyer, P. v. R. Angew. Chem., Int. Ed. Engl. 1979, 18, 939.
- 6 Grubmuller, P.; Maier, W. F.; Schleyer, P. v. R.; McKervey, M. A.; Rooney, J. J. Ber. 1980, 113, 1989.
- 7 Savoia, D.; Tagliavini, E.; Trombini, C.; Umani-Ronchi, A. J. Org. Chem. 1981, 46, 5340.
- 8 Brunet, J. J.; Gallois, P.; Caubere, P. J. Org. Chem. 1980, 45, 1937.
- 9 Ciborowski, S. Przem. Chem. 1960, 39, 228 ( Chem. Abstr. 1961, 55, 4387e).
- 10 Greenfield, H. Ind. Eng. Chem., Prod. Res. Develop. 1967, 6, 142.
- 11 (a) Alonso, F.; Radivoy, G.; Yus, M., Russ. Chem. Bull. 2003, 52, 2563. (b) Alonso, F.; Yus, M., Chem. Soc. Rev. 2004, 33, 284. (c) Alonso, F.; Yus, M., Pure Appl. Chem. 2008, 80, 1005. (d) Alonso, F.; Riente, P.; Yus, M., Acc. Chem. Res. 2011, 44, 379. (e) Yus, M., Rev. Soc. Catalana Quim. 2011, 10, 5. For characterization of NiNPs, see: (f) Alonso, F.; Calvino, J. J.; Osante, I.; Yus, M., Chem. Lett. 2005, 34, 1262. (g) Alonso, F.; Calvino, J. J.; Osante, I.; Yus, M., J. Exper. Nanosci. 2006, 1, 419.
- 12 C. R. Sarco; M. DiMare In Encyclopedia of Reagents for Organic Synthesis; L. A. Paquete, Ed.; Wiley: Chichester, 1995; Vol. 6, pp 3701–3702.
- 13 (a) Alonso, F.; Yus, M., Adv. Synth. Catal. 2001, 343, 188. (b) Alonso, F.; Candela, P.; Gómez, C.; Yus, M., Adv. Synth. Catal. 2003, 345, 275.
- 14 Polshettiwar, V.; Baruwati, B.; Varma, R. S., Green Chem. 2009, 11, 127.
- 15 (a) Alonso, F.; Yus, M., Tetrahedron Lett. 1996, 37, 6925. (b) Alonso, F.; Yus, M., J. Chem. Educ. 2001, 78, 1517.
- 16 Alonso, F.; Yus, M., Tetrahedron Lett. 1997, 38, 149.
- 17 Radivoy, G.; Alonso, F.; Yus, M., Tetrahedron 1999, 55, 14479.
- 18 Hu, Y.; Yu, Y.; Hou, Z.; Yang, H.; Feng, B.; Li, H.; Qiao, Y.; Wang, X.; Hua, L.; Pan, Z.; Zhao, X., Chem. Asian J. 2010, 5, 1178.
- 19 (a) Review: Alonso, F.; Beletskaya, I. P.; Yus, M., Chem. Rev. 2002, 102, 4009. (b) Alonso, F.; Radivoy, G.; Yus, M., Tetrahedron 1999, 55, 4441.
- 20 Alonso, F.; Yus, M., Tetrahedron 1998, 54, 1921.
- 21 (a) Kidwai, M.; Bansal, V.; Saxena, A.; Shankar, R.; Mozumdar, S., Tetrahedron Lett. 2006, 47, 4161. (b) Kidwai, M.; Mishra, N. K.; Bansal, V.; Kumar, A.; Mozumdar, S., Catal. Commun. 2008, 9, 612.
- 22 Alonso, F.; Radivoy, G.; Yus, M., Tetrahedron 2000, 56, 8673.
- 23 Radivoy, G.; Alonso, F.; Yus, M., Synthesis 2001, 427.
- 24 Alonso, F.; Osante, I.; Yus, M., Tetrahedron 2007, 63, 93.
- 25 Dhakshinamoorthy, A.; Pitchumani, K., Tetrahedron Lett. 2008, 49, 1818.
- 26 Alonso, F.; Osante, I.; Yus, M., Adv. Synth. Catal. 2006, 348, 305.
- 27 Alonso, F.; Osante, I.; Yus, M., Synlett 2006, 3017.
- 28 (a) Gómez, C.; Ruiz, S.; Yus, M., Tetrahedron Lett. 1998, 39, 1397. (b) Gómez, C.; Ruiz, S.; Yus, M., Tetrahedron 1999, 55, 7017. (c) Candela, P.; Gómez, C.; Yus, M., Russ. J. Org. Chem. 2004, 40, 795.
- 29 Alonso, F.; Riente, P.; Yus, M., Tetrahedron 2009, 65, 10637.
- 30 Boldrini, G. P.; Savoia, D.; Tagliavini, E.; Trombini, C.; Umani-Ronchi, A., J. Org. Chem. 1985, 50, 3082.
- 31 (a) Alonso, F.; Riente, P.; Yus, M., Tetrahedron Lett. 2008, 49, 1939. (b) Alonso, F.; Riente, P.; Yus, M., Tetrahedron 2008, 64, 1847.
- 32 Park, J. C.; Lee, H. J.; Kim, J. Y.; Park, K. Y.; Song, H., J. Phys. Chem. C 2010, 114, 6381.
- 33 Neelakandeswari, N.; Sangami, G.; Emayavaramban, P.; Babu, S. G., J. Mol. Catal. A Chem. 2012, 356, 90.
- 34 (a) Mohapatra, S. K.; Sonavane, S. U.; Jayaram, R.; Salvam, P., Org. Lett. 2002, 4, 4297. (b) Selvam, P.; Mohapatra, S. K.; Sonovane, S. U.; Jayaram, R. V., Tetrahedron Lett. 2004, 45, 2003.
- 35 Upadhya, T. T.; Sabde, D. P.; Ramaswamy, V.; Sudalai, A., Chem. Commun. 1997, 119.
- 36 Alonso, F.; Riente, P.; Yus, M., Synlett 2008, 1289.
- 37 Alonso, F.; Riente, P.; Sirvent, J. A.; Yus, M., Appl. Catal. A. Gen, 2010, 378, 42.
- 38 (a) Guillena, G.; Ramón, D. J.; Yus, M., Angew. Chem., Int. Ed. 2007, 46, 2358. (b) Guillena, G.; Ramón, D. J.; Yus, M., Chem. Rev. 2010, 110, 1611. (c) Alonso, F.; Foubelo, F.; González-Gómez, J. C.; Martínez, R.; Ramón, D. J.; Riente, P.; Yus, M., Mol. Div. 2010, 14, 411.
- 39 (a) Hamid, M. H. S. A.; Slatford, P. A.; Williams, J. M. J., Adv. Synth. Catal. 2007, 349, 1555. (b) Nixon, T. D.; Whittlesey, M. K.; Williams, J. M. J., Dalton Trans. 2009, 753. (c) Watson, A. J. A.; Williams, J. M. J., Science 2010, 329, 635.
- 40 (a) Alonso, F.; Riente, P.; Yus, M., Synlett 2007, 1877. (b) Alonso, F.; Riente, P.; Yus, M., Eur. J. Org. Chem. 2008, 4908.
- 41 (a) Alonso, F.; Riente, P.; Yus, M., Synlett 2009, 1579. (b) Alonso, F.; Riente, P.; Yus, M., Eur. J. Org. Chem. 2009, 6034. (c) Alonso, F.; Riente, P.; Yus, M., Tetrahedron Lett. 2009, 50, 3070.
- 42 Li, H.; Zhang, R.; Wang, H.; Pan, Y.; Shi, Y., Synth. Commun. 1997, 27 3047.
- 43 Hu, Y.; Yu, Y. Y.; Zhao, X. G.; Yang, H. M.; Feng, B.; Li, H.; Qiao, Y. X.; Hua, L.; Pan, Z. Y.; Hou, Z. S., Sci. China Chem. 2010, 53, 1541.
- 44 Bandgar, B. P.; Uppalla, L. S., J. Chem. Res. (S) 1999, 714.
