Highly selective hydrogenation of multiple carbon-carbon bonds promoted by nickel(0) nanoparticles

Tetrahedron

Volumn 63, Issue 1, 2007, Pages 93-102

  Alonso, Francisco ^a   Osante, Iñaki ^a   Yus, Miguel ^a  

^a UNIVERSITY OF ALICANTE   (Spain)

Author keywords

Alkenes; Alkynes; Dienes; Nickel nanoparticles; Selective hydrogenation

Indexed keywords

ALKADIENE; ALKANE DERIVATIVE; ALKENE DERIVATIVE; ALKYNE DERIVATIVE; CARBON; NICKEL;

ARTICLE; CHEMICAL BOND; HYDROGENATION; NANOPARTICLE; PRIORITY JOURNAL; REDUCTION KINETICS; STEREOCHEMISTRY;

EID: 34547633049     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.10.043     Document Type: Article

References (59)

1. For reviews, see:
2. Siegel S. In: Trost B.M., Fleming I., and Semmelhack M.F. (Eds). Comprehensive Organic Chemistry Vol. 8 (1991), Pergamon, Oxford Chapter 3.1
3. Molnár A., Sárkány A., and Varga M. J. Mol. Catal. A: Chem. 173 (2001) 185-221
4. Nishimura S. Handbook of Heterogeneous Catalytic Hydrogenation for Organic Synthesis (2001), Wiley-Interscience, New York, NY
5. Takaya H., and Noyori R. In: Trost B.M., Fleming I., and Semmelhack M.F. (Eds). Comprehensive Organic Chemistry Vol. 8 (1991), Pergamon, Oxford Chapter 3.2
6. For a general reference, see:
7. Pasto D.J. In: Trost B.M., Fleming I., and Semmelhack M.F. (Eds). Comprehensive Organic Chemistry Vol. 8 (1991), Pergamon, Oxford Chapter 3.3
8. For more specific references, see for instance:
9. Corey E.J., Mock W.L., and Pasto D.J. Tetrahedron Lett. (1961) 347-352
10. Brandsma L., Nieuwenhuizen W.F., Zwikker J.W., and Mäeorg U. Eur. J. Org. Chem. (1999) 775-779
11. Kaufman D., Johnson E., and Mosher M.D. Tetrahedron Lett. 46 (2005) 5613-5615
12. Castro C.E., and Stephens R.D. J. Am. Chem. Soc. 86 (1964) 4358-4363
13. Ohmori K., Hachisu Y., Suzuki T., and Suzuki K. Tetrahedron Lett. 43 (2002) 1031-1034
14. Ashby E.C., and Lin J.J. J. Org. Chem. 43 (1978) 2567-2572
15. Lindlar H. Helv. Chim. Acta 35 (1952) 446-450
16. Lindlar H., and Dubuis R. Org. Synth. Coll. 5 (1973) 880-883
17. Cortese N.A., and Heck R.F. J. Org. Chem. 43 (1978) 3985-3987
18. Gallois P., Brunet J.-J., and Caubère P. J. Org. Chem. 45 (1980) 1946-1950
19. Brunet J.-J., and Caubère P. J. Org. Chem. 49 (1984) 4058-4060
20. Savoia D., Tagliavini E., Trombini C., and Umani-Ronchi A. J. Org. Chem. 46 (1981) 5340-5343
21. Choudary B.M., Sharma G.V.M., and Bharathi P. Angew. Chem., Int. Ed. Engl. 28 (1989) 465-466
22. Choi J., and Yoon N.M. Tetrahedron Lett. 37 (1996) 1057-1060
23. Yoon N.M., Park K.B., Lee H.J., and Choi J. Tetrahedron Lett. 37 (1996) 8527-8528
24. van Laren M.W., and Elsevier C.J. Angew. Chem., Int. Ed. 38 (1999) 3715-3717
25. Gruttadauria M., Noto R., Deganello G., and Liotta L.F. Tetrahedron Lett. 40 (1999) 2857-2858
26. Campos K.R., Cai D., Journet M., Kowal J.J., Larsen R.D., and Reider P.J. J. Org. Chem. 66 (2001) 3634-3635
27. Hudlický M. Reductions in Organic Chemistry. 2nd ed. (1996), ACS, Washington, DC pp 56-57
28. Dahlén A., and Hilmerson G. Tetrahedron Lett. 44 (2003) 2661-2664
29. Hudlický M. Reductions in Organic Chemistry. 2nd ed. (1996), ACS, Washington, DC p 10
30. Paquette L.A. Encyclopedia of Reagents for Organic Synthesis Vol. 6 (1995), Wiley, Chichester, UK p 4401
31. For a recent application of Raney nickel, see for instance:. Okimoto M., Takahashi Y., Nagata Y., Satoh M., Sueda S., and Yamashina T. Bull. Chem. Soc. Jpn. 77 (2004) 1405-1406
32. Alonso F., Calvino J.J., Osante I., and Yus M. Chem. Lett. (2005) 1262-1263
33. Alonso F., and Yus M. Adv. Synth. Catal. 343 (2001) 188-191
34. Alonso F., Candela P., Gómez C., and Yus M. Adv. Synth. Catal. 345 (2003) 275-279
35. Alonso F., and Yus M. Chem. Soc. Rev. 33 (2004) 284-293
36. This system has been recently applied to the selective conjugate reduction of α,β-unsaturated carbonyl compounds: Alonso, F.; Osante, I.; Yus, M. Synlett 3017-3020.
37. Alonso, F.; Osante, I.; Yus, M. J. Exp. Nanosci., in press.
38. Alonso F., Osante I., and Yus M. Adv. Synth. Catal. 348 (2006) 305-308
39. Alonso F., and Yus M. Tetrahedron Lett. 38 (1997) 149-152
40. Gómez C., Ruiz S., and Yus M. Tetrahedron Lett. 39 (1998) 1397-1400
41. Gómez C., Ruiz S., and Yus M. Tetrahedron 55 (1999) 7017-7026
42. Candela P., Gómez C., and Yus M. Russ. J. Org. Chem. 40 (2004) 795-801
43. Brandsma L., and Verkruijsse H.D. Synthesis (1978) 290
44. Brandsma L. Synthesis of Acetylenes, Allenes and Cumulenes: Methods and Techniques (2004), Elsevier, Amsterdam p 215
45. Hudlický M. Reductions in Organic Chemistry. 2nd ed. (1996), ACS, Washington, DC p 270
46. See procedure IV.3 in Ref. 24b.
47. Okada K., Oshima K., and Utimoto K. J. Am. Chem. Soc. 118 (1996) 6076-6077
48. Flippin L.A., Brown P.A., and Jalali-Araghi K. J. Org. Chem. 54 (1989) 3588-3596
49. Courtois G., and Miginiac P. Bull. Soc. Chem. Fr. (1983) 21-27
50. Mostamandi A., Remizova L.A., and Favorskaya I.A. Zh. Org. Khim. 18 (1982) 1559-1560 Chem. Abstr. 1982, 97, 162266
51. Doolittle R.E., Patrick D.J., and Heath R.H. J. Org. Chem. 58 (1993) 5063-5066
52. Taber D.F., Kanai K., and Pina R. J. Am. Chem. Soc. 121 (1999) 7773-7777
53. Azzena F., Calvani F., Crotti P., Gardelli C., Macchia G., and Pineschi M. Tetrahedron 51 (1995) 10601-10626
54. Takeuchi R., Ue N., Tanabe K., Yamashita K., and Shiga N. J. Am. Chem. Soc. 123 (2001) 9525-9534
55. Fedtke C., Depka B., Schallner O., Tietjen K., Trebst A., Wollweber D., and Wroblowsky H.J. Pest. Manag. Sci. 57 (2001) 278-282
56. Midland M., and Koops R.W. J. Org. Chem. 55 (1990) 5058-5065
57. Alonso F., and Yus M. Tetrahedron Lett. 37 (1996) 6925-6928
58. Baig T., Molinier J., and Kalck P. J. Organomet. Chem. 455 (1993) 219-224
59. Sakota N., and Tanaka S. Bull. Chem. Soc. Jpn. 44 (1971) 485-488