A preparation of benzylic and allylic boronates: Cross-coupling of aryl- and alkenylstannanes with bromomethylboronates

Tetrahedron Letters

Volumn 40, Issue 31, 1999, Pages 5647-5650

  Falck, J R ^a   Bondlela, Muralidhar ^a   Ye, Jianhua ^a   Su Dong, Cho ^a  

^a UNIVERSITY OF TEXAS SOUTHWESTERN MEDICAL CENTER   (United States)

Author keywords

Boronates; Coupling reactions; Palladium; Stille

Indexed keywords

BROMINE DERIVATIVE; ORGANOBORON DERIVATIVE; ORGANOTIN COMPOUND; PALLADIUM;

ARTICLE; CATALYSIS; CATALYST; CROSS LINKING; MOLECULAR INTERACTION; SYNTHESIS;

EID: 0033618386     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01136-3     Document Type: Article

References (20)

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3. Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457-2483. Salunkhe, A. M.; Ramachandran, P. V.; Brown, H. C.Tetrahedron Lett. 1999, 40, 1433-1436.
4. Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457-2483. Salunkhe, A. M.; Ramachandran, P. V.; Brown, H. C. Tetrahedron Lett. 1999, 40, 1433-1436.
5. Wuts, P. G.; Tompson, P. A.; Callen, G. R. J. Org. Chem. 1983, 48, 5398-5400. Watanabe, T.; Miyaura, N.; Suzuki, A. J.organometallic Chem. 1993, 444, C1-C3. Kanai, G.; Miyaura, N.; Suzuki, A. Chem. Lett. 1993, 845-848.
6. Wuts, P. G.; Tompson, P. A.; Callen, G. R. J. Org. Chem. 1983, 48, 5398-5400. Watanabe, T.; Miyaura, N.; Suzuki, A. J. Organometallic Chem. 1993, 444, C1-C3. Kanai, G.; Miyaura, N.; Suzuki, A. Chem. Lett. 1993, 845-848.
7. Wuts, P. G.; Tompson, P. A.; Callen, G. R. J. Org. Chem. 1983, 48, 5398-5400. Watanabe, T.; Miyaura, N.; Suzuki, A. J.organometallic Chem. 1993, 444, C1-C3. Kanai, G.; Miyaura, N.; Suzuki, A. Chem. Lett. 1993, 845-848.
8. Wang, K. K.; Liu, C.; Gu, Y. G.; Burnett, F. N. J. Org. Chem. 1991, 56, 1914-1922. Ishiyama, T.; Yamamoto, M.;Miyaura, N. Chem. Commun. 1996, 2073-2074. Satoh, M.; Nomoto, Y.; Miyaura, N.; Suzuki, A. Tetrahedron Lett. 1989, 30, 3789-3792.
9. Wang, K. K.; Liu, C.; Gu, Y. G.; Burnett, F. N. J. Org. Chem. 1991, 56, 1914-1922. Ishiyama, T.; Yamamoto, M.; Miyaura, N. Chem. Commun. 1996, 2073-2074. Satoh, M.; Nomoto, Y.; Miyaura, N.; Suzuki, A. Tetrahedron Lett. 1989, 30, 3789-3792.
10. Wang, K. K.; Liu, C.; Gu, Y. G.; Burnett, F. N. J. Org. Chem. 1991, 56, 1914-1922. Ishiyama, T.; Yamamoto, M.;Miyaura, N. Chem. Commun. 1996, 2073-2074. Satoh, M.; Nomoto, Y.; Miyaura, N.; Suzuki, A. Tetrahedron Lett. 1989, 30, 3789-3792.
11. Alternative methodology: Ishiyama, T.; Ahiko, T.-A.; Miyaura, N. Tetrahedron Lett. 1996, 38, 6889-6892. Sato, M.;Yamamoto, Y.; Hara, S.; Suzuki, A. Tetrahedron Lett. 1993, 34, 7071-7074. Hoffmann, R. W.; Feussner, G.; Zeiss, H.-J.;Schulz, S. J. Organomet. Chem. 1980, 187, 321-329.
12. Alternative methodology: Ishiyama, T.; Ahiko, T.-A.; Miyaura, N. Tetrahedron Lett. 1996, 38, 6889-6892. Sato, M.; Yamamoto, Y.; Hara, S.; Suzuki, A. Tetrahedron Lett. 1993, 34, 7071-7074. Hoffmann, R. W.; Feussner, G.; Zeiss, H.-J.;Schulz, S. J. Organomet. Chem. 1980, 187, 321-329.
13. Alternative methodology: Ishiyama, T.; Ahiko, T.-A.; Miyaura, N. Tetrahedron Lett. 1996, 38, 6889-6892. Sato, M.;Yamamoto, Y.; Hara, S.; Suzuki, A. Tetrahedron Lett. 1993, 34, 7071-7074. Hoffmann, R. W.; Feussner, G.; Zeiss, H.-J.; Schulz, S. J. Organomet. Chem. 1980, 187, 321-329.
14. Under these conditions, alkyl- and alkynylstannanes react sluggishly to give little, if any, homologated boronate.
15. These esters were selected for their hydrolytic stability.
16. Michnick, T. J.; Matteson, D. S. Synlett 1991, 631-632.
17. Sheffy, F. K.; Godschalx, J. P.; Stille, J. K. J. Am. Chem. Soc. 1984, 106, 4833-4839.
18. 4.
19. 3, 400 MHz) of pinanediol boronate 2: δ 7.12-7.32 (m, 5H), 5.38-5.60 (m, 2H), 4.26 (dd, J=1.9, 8.8 Hz, 1H), 2.57-2.63 (m, 2H), 2.29-2.36 (m, 1H), 2.18-2.22 (m, 1H), 2.00-2.12 (m, 3H), 1.80-1.92 (m, 2H), 1.62-1.76 (m, 4H), 1.36-1.40 (m, 3H), 1.27 (s, 3H), 1.16 (d, J=10.7,1H), 0.83 (s, 3H). Pinanediol boronate 14: δ 7.17-7.37 (m, 5H), 6.43 (d, J=11.5 Hz, 1H), 5.80-5.90 (m, 1H), 4.28 (dd, J=1.9, 8.8 Hz, 1H), 2.16-2.40 (m, 2H), 1.98-2.09 (m, 3H), 1.82-1.96 (m, 2H), 1.38 (s, 3H), 1.28 (s, 3H), 1.10 (d, J=10.7 Hz, 1H), 0.84 (s, 3H). Pinanediol boronate 22: δ 7.11 (d, J=8.5 Hz, 2H), 6.80 (d, J=8.5 Hz, 2H), 4.27 (dd, J=1.8, 8.8 Hz, 1H), 3.77 (s, 3H), 2.24-2.36 (m, 3H), 2.14-2.22 (m, 1H), 2.01-2.06 (m, 1H), 1.78-1.92 (m, 2H), 1.37 (s, 3H), 1.27 (s, 3H), 1.06 (d, J=10.6 Hz, 1H), 0.82 (s, 3H).
20. Stannane dimerization was the main reaction in these solvents.