A regio- and stereoselective platinum(0)-catalyzed hydroboration of allenes controlled by phosphine ligands

Chemistry Letters

Volumn , Issue 10, 1999, Pages 1069-1070

  Yamamoto, Yasunori ^a   Fujikawa, Ryou ^a   Yamada, Akihiko ^a   Miyaura, Norio ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0033235144     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1999.1069     Document Type: Article

References (15)

1. For reviews, see: K. Burgess and M. J. Ohlmeyer, Chem. Rev., 91, 1179 (1991). I. Beleskaya and A. Pelter, Tetrahedron, 53, 4957 (1997).
2. For reviews, see: K. Burgess and M. J. Ohlmeyer, Chem. Rev., 91, 1179 (1991). I. Beleskaya and A. Pelter, Tetrahedron, 53, 4957 (1997).
3. D. S. Sethi, G. C. Joshi, and D. Devaprabhakara, Can. J. Chem., 47, 1083 (1969); R. H. Fish, J. Am. Chem. Soc., 90, 4435 (1968); H. C. Brown, R. Liotta, and G. W. Kramer, J. Am. Chem. Soc., 101, 2966 (1979).
4. D. S. Sethi, G. C. Joshi, and D. Devaprabhakara, Can. J. Chem., 47, 1083 (1969); R. H. Fish, J. Am. Chem. Soc., 90, 4435 (1968); H. C. Brown, R. Liotta, and G. W. Kramer, J. Am. Chem. Soc., 101, 2966 (1979).
5. D. S. Sethi, G. C. Joshi, and D. Devaprabhakara, Can. J. Chem., 47, 1083 (1969); R. H. Fish, J. Am. Chem. Soc., 90, 4435 (1968); H. C. Brown, R. Liotta, and G. W. Kramer, J. Am. Chem. Soc., 101, 2966 (1979).
6. 2 (0.03 mmol) was flushed with argon. Toluene (5 ml) and a phosphirie ligand (0.06 mmol) were added to give a catalyst solution. An allène (1.0 mmol) and pinacolboranc (1.5 mmol) were then added to the flask. After being stirred for 2 h at 50 °C, the reaction mixture was concentrated in vacuo. The product was isolated by Kugelrohr distillation or chromatography over silica gel with hexane/ether.
7. K. R. Dunbar and S. C. Haefner, Polyhedron, 13, 727 (1994).
8. 3) δ 0.89 (t, 3H, J= 1.1 Hz), 1.26 (s, 12H), 1.27-1.42 (m, 4H), 1.68 (s, 3H), 2.12 (dt, 2H, J= 7.1 and 6.8 Hz), 6.32 (t, IH, J= 6.8 Hz). A 2% of NOE was observed between two protons at 1.68 and 2.12 ppm.
9. R. W. Hoffmann, B. Kemper, R. Metternich, and T. Lehmeier, Liebigs Ann. Chem., 1985, 2246; P. G. M. Wuts and S. S. Bigelow, J. Org. Chem., 47, 2498 (1982); P. Ganesh and K. M. Nicholas, J. Org. Chem., 62, 1737 (1997).
10. R. W. Hoffmann, B. Kemper, R. Metternich, and T. Lehmeier, Liebigs Ann. Chem., 1985, 2246; P. G. M. Wuts and S. S. Bigelow, J. Org. Chem., 47, 2498 (1982); P. Ganesh and K. M. Nicholas, J. Org. Chem., 62, 1737 (1997).
11. R. W. Hoffmann, B. Kemper, R. Metternich, and T. Lehmeier, Liebigs Ann. Chem., 1985, 2246; P. G. M. Wuts and S. S. Bigelow, J. Org. Chem., 47, 2498 (1982); P. Ganesh and K. M. Nicholas, J. Org. Chem., 62, 1737 (1997).
12. Y. Yamamoto, T. Miyairi, T. Ohmura, and N. Miyaura, J. Org. Chem., 64, 296 (1999).
13. I. Rivera and J. A. Soderquist, Tetrahedron Lett., 32, 2311 (1991).
14. A similar regioselectivity was observed in the diboradon of allenes with bis(pinacolato)diboron: T. Ishiyama, T. Kitano, and N. Miyaura, Tetrahedron Lett., 39, 2357 (1998).
15. "Applied Homogeneous Catalysis with Organometallic Compounds," ed by B. Cornus and W. A Herrmann, VCH, Weinheim (1996), Vol. 1, p. 487.