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Active nickel-based reduction of organic compounds

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Russian Chemical Bulletin Aims and scope

Abstract

The reducing system NiCl2·2H2O—Li—arenecat (cat is catalyst) was proposed for use to reduce a wide range of organic compounds, including alkenes, alkynes, carbonyl compounds, imines, halogenated derivatives, sulfonates, aromatic compounds, hydrazines, azo and azoxy compounds, N-oxides, and nitrones. The degree of reduction can be controlled for some substrates. Deuterium can be incorporated in the reaction products using nickel chloride deuteriohydrate. Nitrones, N-alkoxyamides, and acyl azides are also reduced with the Li—arenecat system containing no nickel salt.

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References

  1. (a) M. Yus, Chem. Soc. Rev., 1996, 25, 155; (b) D. J. Ramón and M. Yus, Eur. J. Org. Chem., 2000, 225; (c) M. Yus, Synlett, 2001, 1197; (d) M. Yus, in The Chemistry of Organolithium Compounds, Eds. Z. Rappoport and I. Marek, Wiley, Chichester, 2003, Ch. 11.

    Google Scholar 

  2. D. Guijarro and M. Yus, Recent Res. Devel. Org. Chem., 1998, 2, 713.

    Google Scholar 

  3. F. Foubelo and M. Yus, Trends Org. Chem., 1998, 7, 1.

    Google Scholar 

  4. (a) C. Nájera and M. Yus, Trends Org. Chem., 1991, 2, 155; (b) C. Nájera and M. Yus, Recent Res. Devel. Org. Chem., 1997, 1, 67; (c) M. Yus and F. Foubelo, Rev. Heteroatom Chem., 1997, 17, 73; (d) C. Nájera and M. Yus, Curr. Org. Chem., 2003, 7, 867.

    Google Scholar 

  5. (a) C. Gómez, S. Ruiz, and M. Yus, Tetrahedron Lett., 1998, 39, 1397; (b) C. Gómez, S. Ruiz, and M. Yus, Tetrahedron, 1999, 55, 7017; (c) M. Yus, C. Gómez, and P. Candela, Tetrahedron, 2002, 58, 6207; (d) T. Arnauld, A. G. M. Barrett, and B. T. Hopkins, Tetrahedron Lett., 2002, 43, 1081.

    Google Scholar 

  6. (a) Comprehensive Organic Synthesis, Eds. B. M. Trost and I. Fleming, Pergamon Press, Oxford, 1991, 8; (b) M. Hudlický, Reductions in Organic Chemistry, American Chemical Society, Washington DC, 1996; (c) p. 53; (d) p. 57; (e) Ch. 9; (f) Ch. 6; (g) p. 131.

    Google Scholar 

  7. (a) P. N. Rylander, Hydrogenation Methods, Academic Press, London, 1985; (b) p. 168; (c) P. A. Chaloner, M. A. Esteruelas, F. Jóo, and L. A. Oro, Homogeneous Hydrogenation, Kluwer Academic Publishers, Dordrech, 1994; (d) S. Nishimura, Handbook of Heterogeneous Catalytic Hydrogenation for Organic Synthesis, Wiley-Interscience, New York, 2001.

    Google Scholar 

  8. (a) S. Siegel, in Comprehensive Organic Synthesis, Eds. B. M. Trost and I. Fleming, Pergamon Press, Oxford, 1991, 8, p. 417; (b) H. Takaya, in Comprehensive Organic Synthesis, Eds. B. M. Trost and I. Fleming, Pergamon Press, Oxford, 1991, 8, p. 443.

    Google Scholar 

  9. D. J. Pasto, in Comprehensive Organic Synthesis, Eds. B. M. Trost and I. Fleming, Pergamon Press, Oxford, 1991, 8, p. 471.

    Google Scholar 

  10. F. Alonso and M. Yus, Tetrahedron Lett., 1996, 37, 6925.

    Google Scholar 

  11. F. Alonso and M. Yus, J. Chem. Educ., 2001, 78, 1517.

    Google Scholar 

  12. F. Alonso and M. Yus, Tetrahedron Lett., 1997, 38, 149.

    Google Scholar 

  13. Comprehensive Organic Synthesis, Eds. B. M. Trost and I. Fleming, Pergamon Press, Oxford, 1991, 8, Ch. 1.1–1.8.

    Google Scholar 

  14. F. Alonso and M. Yus, Tetrahedron, 1998, 54, 1921.

    Google Scholar 

  15. F. Alonso, I. P. Beletskaya, and M. Yus, Chem. Rev., 2002, 102, 4009.

    Google Scholar 

  16. F. Alonso, G. Radivoy, and M. Yus, Tetrahedron, 1999, 55, 4441.

    Google Scholar 

  17. Y. Ueno, C. Tanaka, and M. Okawara, Chem. Lett., 1983, 795.

  18. W. J. Scott and J. E. McMurry, Acc. Chem. Res., 1988, 21, 47.

    Google Scholar 

  19. R. P. Polniaszek and L. W. Dillard, J. Org. Chem., 1992, 57, 4103.

    Google Scholar 

  20. H. Kotsuki, P. K. Datta, H. Hayakawa, and H. Suenaga, Synthesis, 1995, 1348.

  21. (a) L. A. Paquette, C. S. Ra, and S. D. Edmonson, J. Org. Chem., 1990, 55, 2443; (b) B. Dupre and A. I. Meyers, J. Org. Chem., 1991, 56, 3197.

    Google Scholar 

  22. (a) S. Cacchi, E. Morera, and G. Ortar, Org. Synth., 1990, 68, 138; (b) D. M. X. Donnelly, J.-P. Finet, P. J. Guiry, and R. M. Hutchinson, J. Chem. Soc., Perkin Trans. 1, 1990, 2851.

    Google Scholar 

  23. K. Sasaki, M. Sakai, Y. Sakakibara, and K. Takagi, Chem. Lett., 1991, 2017.

  24. G. Radivoy, F. Alonso, and M. Yus, Tetrahedron, 1999, 55, 14479.

    Google Scholar 

  25. A. J. Birch, Pure Appl. Chem., 1996, 68, 553.

    Google Scholar 

  26. P. W. Rabideau, Tetrahedron, 1989, 45, 1579.

    Google Scholar 

  27. K. Briner, in Encyclopedia of Reagents for Organic Synthesis, Ed. L. A. Paquette, Wiley, Chichester, 1995, 5, p. 3003.

    Google Scholar 

  28. A. R. Katritzky, S. Rachwal, and B. Rachwal, Tetrahedron, 1996, 52, 15031.

    Google Scholar 

  29. A. Srikrishna, J. R. Reddy, and R. Viswajanani, Tetrahedron, 1996, 52, 1631.

    Google Scholar 

  30. (a) T. L. Gilchrist, in Comprehensive Organic Synthesis, Eds. B. M. Trost and I. Fleming, Pergamon Press, Oxford, 1991, 8, p. 388; (b) p. 382; (c) p. 390.

    Google Scholar 

  31. (a) A. Alexakis, N. Lensen, and P. Mangeney, Tetrahedron Lett., 1991, 32, 1171; (b) A. Alexakis, N. Lensen, and P. Mangeney, Synlett, 1991, 625.

    Google Scholar 

  32. (a) I. M. Mallor and N. M. Smith, J. Chem. Soc., Perkin Trans 1, 1984, 2927; (b) S. E. Denmark, O. Nicaise, and J. P. Edwards, J. Org. Chem., 1990, 55, 6219.

  33. (a) M. J. Burk and J. E. Feaster, J. Am. Chem. Soc., 1992, 114, 6266; (b) S. Kobayashi and R. Hirabayashi, J. Am. Chem. Soc., 1999, 121, 6942.

    Google Scholar 

  34. (a) B. T. Newbold, in The Chemistry of the Hydrazo, Azo, and Azoxy Groups, Ed. S. Patai, Wiley, New York, 1975; (b) S. R. Sandler and W. Karo, in Organic Functional Group Preparations, Academic Press, Orlando, 1983, 1, p. 452.

    Google Scholar 

  35. (a) A. Hajós, Methoden der Organischen Chemie (Houben-Weyl), 1980, IV/1d, 1; (b) J. M. Pratt and G. Swinden, J. Chem. Soc., Chem. Commun., 1969, 1321; (c) J. Lehmann, Methoden der Organischen Chemie (Houben-Weyl), 1980, IV/1c, 482.

    Google Scholar 

  36. (a) K. K. Park and S. Y. Han, Tetrahedron Lett., 1996, 37, 6721; (b) M. L. Patil, G. K. Jnaneschwara, D. P. Sabde, M. K. Dongare, A. Sudalai, and V. H. Deshpande, Tetrahedron Lett., 1997, 38, 2137.

    Google Scholar 

  37. J. Bracht, Methoden der Organischen Chemie (Houben-Weyl), 1981, IV/1d, 575.

    Google Scholar 

  38. W. Adam, J. N. Moorthy, W. M. Nau, and J. C. Scaiamo, J. Am. Chem. Soc., 1997, 119, 6749.

    Google Scholar 

  39. G. Belot and C. Degrand, Tetrahedron Lett., 1976, 17, 153.

    Google Scholar 

  40. (a) A. G. Hortmann, J. Koo, and C.-C. Yu, J. Org. Chem., 1978, 43, 2289; (b) H. Alper and M. Gopal, J. Org. Chem., 1981, 46, 2593; (c) R. Sánchez, G. Vest, W. Scott, and P. S. Engel, J. Org. Chem., 1989, 54, 4026.

    Google Scholar 

  41. Y. He, H. Zhao, X. Pan, and S. Wang, Synth. Commun., 1989, 19, 3047.

    Google Scholar 

  42. A. Albini and S. Pietra, Heterocyclic N-Oxides, CRC, Boca Raton, 1991.

    Google Scholar 

  43. E. C. Taylor, A. J. Crovetti, and N. E. Boyer, J. Am. Chem. Soc., 1957, 79, 3549; (b) J. A. Berson and T. Cohen, J. Org. Chem., 1955, 20, 1461.

    Google Scholar 

  44. (a) T. B. Sim, J. H. Ahn, and N. M. Yoon, Synthesis, 1996, 324; (b) K. P. Chary, G. H. Mohan, and D. S. Iyengar, Chem. Lett., 1999, 1339; (c) D. K. Dutta and D. Konwar, J. Chem. Res. (S), 1998, 266; (d) R. Balicki, Synthesis, 1989, 645.

  45. H. C. Brown and B. C. Subba Rao, J. Am. Chem. Soc., 1956, 78, 2582.

    Google Scholar 

  46. (a) G. A. Olah, M. Arvanaghi, and Y. D. Vankar, Synthesis, 1980, 660; (b) T. Morita, K. Kuroda, Y. Okamoto, and H. Sakurai, Chem. Lett., 1981, 921.

  47. F. Alonso, G. Radivoy, and M. Yus, Tetrahedron, 2000, 56, 8673.

    Google Scholar 

  48. T. R. van den Ancker and C. L. Raston, J. Organomet. Chem., 1998, 550, 283.

    Google Scholar 

  49. (a) J. Hamer and A. Macaluso, Chem. Rev., 1964, 64, 473; (b) A. Jeevanamdam, C. Cartwright, and Y.-C. Ling, Synth. Commun., 2000, 30, 3153.

    Google Scholar 

  50. W. R. Bowman and R. J. Marmon, in Comprehensive Organic Functional Group Transformations, Eds. A. R. Katritzky, O. Meth-Cohn, C. W. Rees, and S. V. Ley, Elsevier Science, Oxford, 1995, 2, p. 344.

    Google Scholar 

  51. G. Radivoy, F. Alonso, and M. Yus, Synthesis, 2001, 427.

  52. (a) S. L. Graham and T. H. Scholz, Tetrahedron Lett., 1990, 31, 6269; (b) G. E. Keck, S. F. McHardy, and J. A. Murry, Tetrahedron Lett., 1993, 34, 6215.

    Google Scholar 

  53. (a) P. G. Mattingly and M. J. Miller, J. Org. Chem., 1980, 45, 410; (b) A. R. Ritter and M. J. Miller, J. Org. Chem., 1994, 59, 4602; (c) G. E. Keck, T. T. Wager, and S. F. McHardy, Tetrahedron, 1999, 55, 11755.

    Google Scholar 

  54. M. Yus, G. Radivoy, and F. Alonso, Synthesis, 2001, 914.

  55. (a) H. S. P. Rao, K. S. Reddy, K. Turnbull, and V. Borchers, Synth. Commun., 1992, 22, 1339; (b) B. C. Ranu, A. Savkar, and R. Chakraborty, J. Org. Chem., 1994, 59, 4114; (c) D. M. Krein, P. J. Sullivan, and K. Turnbull, Tetrahedron Lett., 1996, 37, 7213.

    Google Scholar 

  56. A. R. Ramesha, S. Bhat, and S. Chandrasekaran, J. Org. Chem., 1995, 60, 7682.

    Google Scholar 

  57. A. Kamal, N. Venugopal Rao, and E. Laxman, Tetrahedron Lett., 1997, 38, 6945.

    Google Scholar 

  58. (a) M. Baruah, A. Boruah, D. Prajapati, J. S. Sandhu, and A. C. Ghosh, Tetrahedron Lett., 1996, 37, 4559; (b) A. Boruah, M. Baruah, D. Prajapati, and J. S. Sandhu, Synlett, 1997, 1253.

    Google Scholar 

  59. D. Pathak, D. D. Laskar, D. Prajapati, and J. S. Sandhu, Chem. Lett., 2000, 816.

  60. (a) F. Alonso and M. Yus, Adv. Synth. Catal., 2001, 343, 188; (b) F. Alonso, P. Candela, C. Gómez, and M. Yus, Adv. Synth. Catal., 2003, 345, 275.

    Google Scholar 

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Authors and Affiliations

  1. Department of Organic Chemistry, Faculty of Sciences, Alicante University, Apdo. 99, E-03080, Alicante, Spain

    F. Alonso & M. Yus

  2. Department of Chemistry, Institute of Research in Organic Chemistry (INIQO), National Southern University, 1253 Alem, 8000, Bahía Blanca, Argentina

    G. Radivoy

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  1. F. Alonso
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Alonso, F., Radivoy, G. & Yus, M. Active nickel-based reduction of organic compounds. Russian Chemical Bulletin 52, 2563–2576 (2003). https://doi.org/10.1023/B:RUCB.0000019874.01782.b4

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