An excellent nickel boride catalyst for the cis-selective semihydrogenation of acetylenes

Tetrahedron Letters

Volumn 37, Issue 7, 1996, Pages 1057-1060

  Choi, Jaesung ^a   Yoon, Nung Min ^a  

^a Sogang University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030065663     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(95)02347-X     Document Type: Article

References (23)

1. (a) Friefelder, M. Practical Catalytic Hydrogenation; Wiley-Interscience: New York, 1971.
2. (b) Rylander, P. Hydrogenation Methods; Academic Press: New York, 1985.
3. Mori, K. The Synthesis of Insect Pheromones. In The Total Synthesis of Natural Products; ApSimon, J., Ed.; Wiley Interscience: New York, 1981; Vol. 4, p 1.
4. See, for example: (a) Bartlett, P. A. Tetrahedron 1980, 36, 3.
5. (b) Ackroyd, J.; Scheinmann, F. Chem. Soc. Rev. 1982, 11, 321.
6. (a) Brown, H. C.; Brown, C. A. J. Am. Chem. Soc. 1963, 85, 1005.
7. (b) Brown, C. A.; Ahuja, V. K. J. Chem. Soc., Chem. Commun. 1973, 553.
8. (c) Brown, C. A.; Ahuja, V. K. J. Org. Chem. 1973, 38, 2226.
9. Brunet, J. J.; Gallois, P.; Caubere, P. J. Org. Chem. 1980, 45, 1937.
10. (a) Lindlar, H. Helv. Chim. Acta 1952, 35, 446.
11. (b) Lindlar, H.; Dubuis, R. Org. Synth.1966, 46, 89.
12. Brunet, J. J.; Caubere, P. J. Org. Chem. 1984, 49, 4058.
13. Ulan, J. G.; Maier, W. F. J. Org. Chem. 1987, 52, 3132.
14. (a) Choudary, B. M.; Sharma, G. V. M.; Bharathi, P. Angew. Chem. Int. Ed. Engl. 1989, 28, 465.
15. (b) Sharma, G. V. M.; Choudary, B. M.; Ravichandra Sarma, M.; Koteswara Rao, K. J. Org. Chem. 1989, 23, 2997.
16. - per gram. The dried resin was stored under nitrogen in refrigerator (∼ 4°C). The hydride content was constant over 6 weeks.
17. (a) Yoon, N. M.; Lee, H. J.; Ahn, J. H.; Choi, J. J. Org. Chem. 1994, 59, 4687.
18. (b) Yoon, N. M.; Choi, J.; Lee, H. J. Bull. Korean Chem.Soc. 1993, 14, 543.
19. (c) Yoon, N. M.; Choi, J. Synlett 1993, 135.
20. (d) Yoon, N. M.; Choi, J.; Shon, Y. S. Synth. Commun. 1993, 23, 3047.
21. Three successive semihydrogenations of 2-butyne-1,4-diol could be carried out over the same catalyst, all in 1.0 h; however, the rate dropped sharply thereafter.
22. 2B, BER decomposes slowly in methanol evolving hydrogen. Therefore, the hydrogenation proceeds without supply of external hydrogen; however the hydrogenation is very slow. For example the hydrogénation of 2-butyne-1,4-diol proceeds only 24% in 1 h and 60% in 6 h.
23. Overhydrogenated propylbenzene (9%) and isomerized trans-1-phenyl-1-propene (1%) were observed together with 90% of cis1-1-phenyl-1-propene in 60 min.