Efficient olefin diboration by a base-free platinum catalyst

Organometallics

Volumn 16, Issue 13, 1997, Pages 2757-2759

  Iverson, Carl N ^a   Smith III, Milton R ^a  

^a MICHIGAN STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 6144254329     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om970199x     Document Type: Article

References (17)

1. For a review, see: Burgess, K.; Ohlmeyer, M. J. Chem. Rev. 1991, 91, 1179-1191.
2. Ishiyama, T.; Matsuda, N.; Miyaura, N.; Suzuki, A. J. Am. Chem. Soc. 1993, 115, 11018-11019.
3. Ishiyama, T.; Matsuda, N.; Murata, M.; Ozawa, F.; Suzuki, A.; Miyaura, N. Organometallics 1996, 15, 713-720.
4. For catalytic additions of B-Sn bonds to alkynes, see: Onozawa, S.; Hatanaka, Y.; Sakakura, T.; Shimada, S.; Tanaka, M. Organometallics 1996, 15, 5450-5452.
5. For catalytic additions of B-Si to alkynes, see: Suginome, M.; Nakamura, H.; Ito, Y. J. Chem. Soc., Chem. Commun. 1996, 2777-2778.
6. Pt(0)-catalyzed additions of B-B bonds to alka-1,3-dienes has been recently reported, see: Ishiyama, T.; Yamamoto, M.; Miyaura, N. J. Chem. Soc., Chem. Commun. 1996, 2073-2074.
7. Baker, R. T.; Nguyen, P.; Marder, T. B.; Westcott, S. A. Angew. Chem., Int. Ed. Engl. 1995, 34, 1336-1337.
8. Iverson, C. N.; Smith, M. R., III. Organometallics 1996, 15, 5155-5165.
9. Marder and co-workers have drawn similar conclusions regarding the mechanism of alkyne diboration, see: Lesley, G.; Nguyen, P.; Taylor, N. J.; Marder, T. B.; Scott, A. J.; Clegg, W.; Norman, N. C. Organometallics 1996, 15, 5127-5154.
10. Green, M.; Howard, J. A. K.; Spencer, J. L.; Stone, F. G. A. J. Chem. Soc., Dalton Trans. 1977, 271-277.
11. Iverson, C. N.; Smith, M. R., III. J. Am. Chem. Soc. 1995, 117, 4403-4404.
12. 13C NMR and mass spectrometry. See the Supporting Information for details.
13. 2 were weighed into a Schlenk flask. 4-Vinylanisole (148 mg, 1.10 mmol), dissolved in 3 mL of toluene, was then added to the solids in the flask. After the reaction mixture was stirred for 30 min at room temperature, the solvent was removed in vacuo and the crude product collected.
14. 2 gave cleaner products, except in diborations of norbornene and norbornadiene.
15. Diboration can be catalyzed in related Pt systems, see: Miyaura, N. Hokkaido University, personal communication, 1997.
16. An excellent review of Pd-catalyzed cross-couplings of boronic acids has recently appeared, see: Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457-2483.
17. The crude diboryl product in entry 2 can be converted to 1,2-hexanediol (46% yield based on starting olefin) when subjected to a basic oxidative workup.