Palladium-catalyzed borylstannylative carbocyclization of diynes and an enyne compound

Organometallics

Volumn 16, Issue 25, 1997, Pages 5389-5391

  Onozawa, Shun Ya ^a   Hatanaka, Yasuo ^a   Choi, Nami ^a   Tanaka, Masato ^a  

^a NATL INST OF MAT AND CHEM RES   (Japan)

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[No Author keywords available]

Indexed keywords

EID: 0000521623     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om970704q     Document Type: Article

References (20)

1. (a) Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635.
2. (b) Trost, B. M. Acc. Chem. Res. 1990, 23, 34.
3. (c) Schore, N. E. Chem. Rev. 1988, 88, 1081.
4. (d) Vollhardt, K. P. C. Angew. Chem., Int. Ed. Engl. 1984, 23, 539.
5. Onozawa, S.-y.; Hatanaka, Y.; Tanaka, M. Chem. Commun. 1997, 1229.
6. (a) Chatani, N.; Morimoto, T.; Muto, T.; Murai, S. J. Organomet. Chem. 1994, 473, 335.
7. (b) Tamao, K.; Kobayashi, K.; Ito, Y. J. Am. Chem. Soc. 1989, 111, 6478.
8. (c) Chatani, N.; Takeyasu, T.; Horiuchi, N.; Hanafusa, T. J. Org. Chem. 1988, 53, 3539.
9. Ojima, I.; Donovan, R. J.; Shay, W. R. J. Am. Chem. Soc. 1992, 114, 6580.
10. Obora, Y.; Tsuji, Y.; Kakeshi, T.; Kobayashi, M.; Shinkai, Y.; Ebihara, M.; Kawamura, T. J. Chem. Soc., Perkin Trans, 1 1995, 599.
11. Onozawa, S.-y.; Hatanaka, Y.; Sakakura, T.; Shimada, S.; Tanaka, M. Organometallics 1996, 15, 5450.
12. Suginome, M.; Nakamura, H.; Ito, Y. Chem. Commun. 1996, 2777.
13. Borylstannane 1 can be easily prepared according to the literature procedure. See: Niedenzu, K.; Rothgery, E. F. Synth. Inorg. Met.-Org. Chem. 1972, 2, 1.
14. A part of this work was presented at the 43rd Symposium on Organometallic Chemistry, Osaka, Japan, Oct 31-Nov 1,1996; Kinki Chemical Society: Osaka, Japan, 1996; Abstract PB231.
15. 2Sn: C, 47.65; H, 7.71; N, 7.94. Found: C, 48.00; H, 7.86; N, 8.04.
16. The stereochemistry of the diene moiety was confirmed by NOE experiments, in which irradiation at allylic protons in the ring resulted in enhancement of vinylic proton (or allylic protons in the side chain for 3f) signals, as shown in Chart 1.
17. 1H NMR yield (97%).
18. w = 0.0820, and GOF = 0.856.
19. Johnson, C. K. ORTEP, a FORTRAN Thermal-Ellipsoid Plot Program for Crystal Structure Illustrations; Report ORNL-3794; Oak Ridge National Laboratory: Oak Ridge, TN, 1970.
20. 4Sn: C, 48.14; H, 7.47; N, 5.61. Found C, 48.24; H, 7.67; N, 5.50.