A versatile synthesis of 9-BBN derivatives from organometallic reagents and 9-(triisopropylsilyl)thio-9-borabicyclo[3.3.1]nonane

Tetrahedron Letters

Volumn 41, Issue 19, 2000, Pages 3537-3539

  Soderquist, John A ^a   Justo De Pomar, Jorge C ^a  

^a UNIVERSITY OF PUERTO RICO RIO PIEDRAS   (Puerto Rico)

Author keywords

[No Author keywords available]

Indexed keywords

ALKANE DERIVATIVE; LITHIUM DERIVATIVE; ORGANOMETALLIC COMPOUND;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; COMPLEX FORMATION; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; SYNTHESIS;

EID: 0342699508     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00450-0     Document Type: Article

References (20)

1. Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
2. (b) Matos, K.; Soderquist, J. A. J. Org. Chem. 1998, 63, 461.
3. (c) Suzuki, A. J. Organomet. Chem. 1999, 576, 147.
4. Pelter, A.; Smith, K.; Brown, H. C. In Borane Reagents; Academic Press Inc.: San Diego, 1988.
5. (b) Soderquist, J. A. In Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A., Ed.; J. Wiley & Sons Ltd: London, 1995; Vol. 1, pp. 622-630.
6. Kramer, G. W.; Brown, H. C. J. Organomet. Chem. 1974, 73, 1. See also: ibid, idem 1977, 132, 9. See also
7. Kramer, G. W.; Brown, H. C. J. Organomet. Chem. 1974, 73, 1. See also: ibid, idem 1977, 132, 9. See also
8. (b) Hennion, G. F.; McCusker, P. A.; Rutkowski, A. J. J. Am. Chem. Soc. 1958, 80, 617.
9. (c) McCusker, P. A.; Marra, J. V.; Hennion, G. F. J. Am. Chem. Soc. 1961, 83, 1924.
10. (d) Hennion, G. A.; McCusker, P. A.; Ashby, E. C.; Rutkowski, A. J. J. Am. Chem. Soc. 1973, 93, 2802.
11. Brown, H. C.; Sinclair, J. A. J. Organomet. Chem. 1977, 131, 163.
12. (b) Brown, H. C.; Bhat, N. G.; Rajagopalan, S. Organometallics 1986, 5, 816.
13. (c) However, B-SMe derivatives give alkynylboranes without added Lewis acids upon warming to 25°C. Pelter, A.; Hughes, R. J.; Smith, K.; Tabata, M. Tetrahedron Lett. 1976, 4385.
14. Singleton, D. A.; Martinez, J. P. J. Am. Chem. Soc. 1990, 112, 7423.
15. (b) Whiteley, C. G. S. Afr. J. Chem. 1982, 35, 9.
16. (c) Soderquist, J. A. In Encyclopedia of Inorganic Chemistry; King, R. B., Ed.; J. Wiley & Sons Ltd: London, 1994; Vol. 1, pp. 401-433.
17. Köster, R.; Seidel, G.; Boese, R. Chem. Ber. 1988, 121, 1137.
18. Soderquist, J. A.; Negron, A. Org. Synth. 1991, 70, 169.
19. (b) Miranda, E. I.; Díaz, M. J.; Rosado, I.; Soderquist, J. A. Tetrahedron Lett. 1994, 35, 3221.
20. Representative procedures: (RLi) To a solution of 1 (1.24 g, 4.0 mmol) in dry ethyl ether (10 mL) at -78°C was added t-BuLi (3.4 mL, 1.6 M). After 45 min, concentration and distillation (head temp. 52-55°C, 3 torr) gave 0.50 g (72%) of 1h. (RMgX) To a solution of 1 (1.52 g, 4.8 mmol) in dry THF (10 mL) at 0°C was added n-BuMgBr (2.75 mL, 2.0 M in THF) dropwise. After 45 min, the system was allowed to reach 25°C, the solvents were removed in vacuo, and heating as above (92-95°C at 5 torr) gave 0.72 g (84%) of pure 1g.