A study of hydroboration of alkenes and alkynes with pinacolborane catalyzed by transition metals

Tetrahedron Letters

Volumn 37, Issue 19, 1996, Pages 3283-3286

  Pereira, Schubert ^a,b   Srebnik, Morris ^a  

^a UNIVERSITY OF TOLEDO   (United States)

^b Fresh Products Inc   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ORGANOBORON DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0029947251     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00576-X     Document Type: Article

References (24)

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2. (b) For a review of uncatalyzed hydroborations with CBH: Pelter, A.; Smith, K.; Brown, H.C. Borane Reagents; in Best Synthetic Methods; Katritzky, A.R.; Meth-Cohn, O.; Rees, C.W., Eds.; Academic Press: London, 1988; p 194.
3. (a) Männig, D.; Nöth, H. Angew. Chem. Int. Ed. Engl. 1985, 24, 878.
4. (b) For a review: Burgess, K.; Ohlmeyer, M.J. Chem. Rev. 1991, 91, 1179.
5. For instance, see the study by: Evans, D.A.; Fu, G.C.; Anderson. B. A. J. Am. Chem. Soc. 1992, 114, 6679.
6. Brown, J.M.; Lloyd-Jones, G.C. J. Am. Chem. Soc. 1994, 116, 866.
7. Burgess, K.; van der Donk, W.A.; Westcott, S.A.; Marder, T.B.; Baker, R.T.; Calabrese, J.C. J. Am. Chem. Soc. 1992, 114, 9350.
8. Wescott, S.A.; Blom, H.P.; Marder, T.B.; Baker, R.T.; Calabrese, J.C. Inorg. Chem. 1993, 32, 2175.
9. Pereira, S.; Srebnik, M. Organometallics 1995, 14, 3127.
10. Pereira, S.; Srebnik, M. J. Am. Chem. Soc. 1996, 118, 909. See also reference 4.
11. (a) Woods, W.G.; Strong, P.L. J. Am. Chem. Soc. 1966, 88, 4667.
12. (b) Tucker, C.E.; Davidson, J.; Knochel, P. J. Org. Chem. 1992, 57, 3482.
13. 3Cl catalyzed hydroborations, the reactions were quenched after 18 h for both alkynes and alkenes.
14. (a) For hydroboration of imines with copper and silver salts: Baker, R.T.; Calabrese, J.C.; Westccott. J. Organomet. Chem. 1995, 498, 109. However, nickel has been used in coupling reactions involving boron:
15. (b) Mizojiri, R.; Kobayashi, Y. J. Chem. Soc. Perkin Trans. 1 1995, 2073.
16. (c) Kobayashi, Y.; Mizojiri, R.; Ikeda, E. Synlett 1995, 571.
17. (d) Trost, B.M.; Spagnol, M.D. J. Chem. Soc. Perkin Trans. 1 1995, 2083.
18. 3 were not effective or gave complex reaction mixtures in the present study.
19. For factors affecting syn-elimination: Mikhailov, B.M.; Bubnov, Yu. N. Organoboron Compounds in Organic Synthesis; Hardwood: Chur, 1984; p 117.
20. (a) Zheng, B.; Srebnik, M. Tetrahedron Lett. 1994, 55, 1145.
21. (b) For reviews of α-halo boronates: Matteson, D.S. Acc. Chem. Res. 1988, 21, 294.
22. (c) Matteson, D.S. Tetrahedron 1989, 45, 1859.
23. (d) Matteson, D.S. Chem. Rev. 1989, 1535.
24. For a study of the course of the reaction with vinyl chlorides in non-catalyzed hydroboration: Brown, H.C; Sharp. R.L. J. Am. Chem. Soc. 1968, 90, 2915, and references cited.