Suzuki reactions with B-allyl-9-borabicyclo[3.3.1]nonane (B-allyl-9-BBN)

Synlett

Volumn , Issue 2, 1998, Pages 161-162

  Fürstner, Alois ^a   Seidel, Günter ^a  

^a MAX PLANCK INSTITUT FÜR KOHLENFORSCHUNG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0003173630     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-1590     Document Type: Article

References (27)

1. Review: Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
2. For some recent developments see: (a) Darses, S.; Genêt, J.-P.; Brayer, J.-L.; Demoute, J.-P. Tetrahedron Lett. 1997, 4393.
3. (b) Giroux, A.; Han, Y.; Prasit, P. Tetrahedron Lett. 1997, 3841.
4. (c) Indolese, A. F. Tetrahedron Lett. 1997, 3513.
5. (d) Sengupta, S.; Bhattacharyya, S. J. Org. Chem. 1997, 62, 3405.
6. (e) Andersen, N. G.; Maddaford, S. P.; Keay, B. A. J. Org. Chem. 1996, 61, 9556.
7. (f) Hildebrand, J. P.; Marsden, S. P. Synlett 1996, 893.
8. (g) Reetz, M. T.; Breinbauer, R.; Wanninger, K. Tetrahedron Lett. 1996, 4499.
9. (h) Saito, S.; Sakai, M.; Miyaura, N. Tetrahedron Lett. 1996, 2993.
10. (i) Beller, M.; Fischer, H.; Herrmann, W. A.; Öfele, K.; Broßmer, C. Angew. Chem. 1995, 107, 1992 and lit. cited.
11. Applied Homogeneous Catalysis with Organometallic Compounds (Cornils, B.; Herrmann, W. A., Eds.), VCH, Weinheim, 1996, Vol. 2.
12. (a) Fürstner, A.; Seidel, G. Tetrahedron 1995, 51, 11165.
13. (b) For a similar concept see: Soderquist, J. E.; Matos, K.; Rane, A.; Ramos, J. Tetrahedron Lett. 1995, 2401.
14. For other applications of the Suzuki reaction from our laboratory see: (a) Fürstner, A.; Seidel, G. J. Org. Chem. 1997, 62, 2332.
15. (b) Fürstner, A.; Konetzki, I. Tetrahedron 1996, 52, 15071.
16. (c) Fürstner, A.; Nikolakis, K. Liebigs Ann. 1996, 2107.
17. (d) Fürstner, A.; Seidel, G.; Gabor, B.; Kopiske, C.; Krüger, C.; Mynott, R. Tetrahedron 1995, 51, 8875.
18. 1, p. 2476.
19. Kalinin, V. N.; Denisov, F. S.; Bubnov, Y. N. Mendeleev Commun. 1996, 206.
20. (a) Kramer, G. W.; Brown, H. C. J. Organomet. Chem. 1977, 132, 9.
21. (b) For a review see: Yamamoto, Y. in Encyclopedia of Reagents for Organic Synthesis (Paquette, L. A., Ed.), Wiley, New York, 1995, 90.
22. It is important to use exactly 1.0 equiv. of KOMe per mole of B-alIyl-9-BBN; an excess of the base may cause allyl → 1-propenyl isomerisations under the reaction conditions.
23. (a) Echavarren, A. M.; Stille, J. K. J. Am. Chem. Soc. 1987, 109, 5478.
24. (b) Farina, V.; Krishnan, B. J. Am. Chem. Soc. 1991, 113, 9585.
25. (c) For a timely and comprehensive review see: Farina, V.; Krishnamurthy, V.; Scott, W. J. Org. React. 1997, 50, 1.
26. For a leading reference on transition metal catalyzed reactions using other allylmetal reagents see: Hayashi, T.; Konishi, M.; Yokata, K-I.; Kumada, M. J. Organomet. Chem. 1985, 285, 359 and lit. cited.
27. 2): calcd. 464.20551; found 464.20384.