Highly stereo- and regioselective synthesis of (Z)-trisubstituted alkenes via 1-bromo-1-alkyne hydroboration-migratory insertion-Zn-promoted iodinolysis and Pd-catalyzed organozinc cross-coupling

Journal of the American Chemical Society

Volumn 129, Issue 47, 2007, Pages 14788-14792

  Huang, Zhihong ^a   Negishi, Ei Ichi ^a  

^a PURDUE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; BORON COMPOUNDS; REGIOSELECTIVITY; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

ALKYNES; CROSS COUPLING REACTIONS; HYDROBORATION; IODINOLYSIS;

OLEFINS;

ALKENE; BORANE DERIVATIVE; PALLADIUM; ZINC;

ARTICLE; CROSS COUPLING REACTION; HYDROBORATION; LITHIATION; REACTION ANALYSIS; STEREOCHEMISTRY; SUZUKI REACTION; SYNTHESIS;

ALKENES; BORON COMPOUNDS; BROMINE COMPOUNDS; CATALYSIS; CROSS-LINKING REAGENTS; HYDROGEN; IODINE; MOLECULAR STRUCTURE; PALLADIUM; STEREOISOMERISM; ZINC;

EID: 36748999337     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0772039     Document Type: Article

References (40)

1. (a) Hassfeld, J.; Farès, C.; Steinmetz, H.; Carlomagno, T.; Menche, D. Org. Lett. 2006, 8, 4751.
2. (b) Menche, D.; Hassfeld, J.; Li, J.; Rudolph, S. J. Am. Chem. Soc. 2007, 129, 6100.
3. Still, W. C.; Gennari, C. Tetrahedron Lett. 1983, 24, 4405.
4. (a) Horner, L.; Hoffmann, H.; Wippel, H. G.; Klahre, G. Chem. Ber. 1959. 92, 2499.
5. (b) Wadsworth, W. S., Jr.; Emmons, W. D. J. Am. Chem. Soc. 1961, 83, 1733.
6. (a) Zweifel, G.; Arzoumanian, H. J. Am. Chem. Soc. 1967, 89, 5086.
7. (b) Chen, Y. K.; Walsh, P. J. J. Am. Chem. Soc. 2004, 126, 3702.
8. (a) Negishi, E.; Yoshida, T. J. Chem. Soc. Chem. Commun. 1973, 606.
9. (b) For its application to the synthesis of (E)-1,4-disubstituted 1,2,3-butatrienes, see: Yoshida, T.; Williams, R. M.; Negishi, E. J. Am. Chem. Soc. 1974, 96, 3688.
10. For the synthesis of (E,Z)-1,4-disubstituted conjugated dienes, see: (a) Negishi, E.; Lew, G.; Yoshida, T. J. Chem. Soc. Chem. Commun. 1973, 874.
11. (b) Negishi, E.; Abramovitch, A. Tetrahedron Lett. 1977, 411.
12. Baba, S.; Negishi, E. J. Am. Chem. Soc. 1976, 98, 6729.
13. (a) Negishi, E.; Okukado, N.; King, A. O.; Van Horn, D. E.; Spiegel, B. I. J. Am. Chem. Soc. 1978, 100, 2254.
14. (b) Negishi, E.; Takahashi, T.; Baba, S.; Van Horn, D. E.; Okukado, N.; Luo, F. T. J. Am. Chem. Soc. 1987, 109, 2393.
15. King, A. O.; Okukado, N.; Negishi, E. J. Chem. Soc. Chem. Commun. 1977, 683.
16. Okukado, N.; Van Horn, D. E.; Klima, W. L.; Negishi, E. Tetrahedron Lett. 1978, 1027.
17. Miyaura, N.; Yamada, K.; Suzuki, A. Tetrahedron Lett. 1979, 20, 3437.
18. (b) For a review, see: Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
19. (a) Jabri, N.; Alexakis, A.; Normant, J. F. Tetrahedron Lett. 1981, 22, 959.
20. (b) Jabri, N.; Alexakis, A.; Normant, J. F. Tetrahedron Lett. 1982, 23, 1589.
21. (a) Stille, J. K.; Groh, B. L. J. Am. Chem. Soc. 1987, 109, 813.
22. (b) For a review, see: Farina, V.; Krishnamurthy, V.; Scott, W. J. Org. React. 1997, 50, 1.
23. For reviews containing discussions of Pd-, Ni-catalyzed cross-coupling with other metals, see: (a) Negishi, E., Ed. Handbook of Organopalladium Chemistry for Organic Synthesis, 2 Vols.; Wiley-Interscience: New York, 2002, Part III, pp 215-1119.
24. (b) de Meijere, A.; Diederich, F., Eds. Metal-Catalyzed Cross-Coupling Reactions, 2 Vols.; Wiley-VCH: Weinheim, 2004, p 916.
25. Satoh, M.; Miyaura, N.; Suzuki, A. Chem. Lett. 1986, 1329.
26. (a) Langer, F.; Schwink, L.; Devasagayaraj, A.; Chavant, P. Y.; Knochel, P. J. Org. Chem. 1996, 61, 8229.
27. (b) Oppolzer, W.; Radinov, R.; Brabander, J. D. Tetrahedron Lett. 1995, 36, 2607.
28. (a) Smith, A. B., III; Qiu, Y.; Jones, D. R.; Kobayashi, K. J. Am. Chem. Soc. 1995, 117, 12011.
29. (b) Harried, S. S.; Yang, G.; Strawn, M. A.; Myles, D. C. J. Org. Chem. 1997, 62, 6098.
30. (c) Marshall, J. A.; Johns, B. A. J. Org. Chem. 1998, 63, 7885.
31. (d) Paterson, I.; Florence, G. J.; Gerlach, K.; Scott, J. Angew. Chem. Int. Ed. 2000, 39, 377.
32. (a) Murakami, N.; Wang, W.; Aoki, M.; Tsutsui, Y.; Sugimoto, M.; Kobayashi, M. Tetrahedron Lett. 1998, 39, 2349.
33. (b) Smith, A. B., III.; Brandt, B. M. Org. Lett. 2001, 3, 1685.
34. (c) Kalesse, M.; Quitschalle, M.; Khandavalli, C. P.; Saeed, A. Org. Lett. 2001, 3, 3107.
35. (d) Marshall, J. A.; Bourbeau, M. P. J. Org. Chem. 2002, 67, 2751.
36. (e) Lautens, M.; Stammers, T. A. Synthesis 2002, 1993.
37. (f) Langille, N. F.; Panek, J. S. Org. Lett. 2004, 6, 3203.
38. Arefolov, A.; Langille, N. F.; Panek, J. S. Org. Lett. 2001, 3, 3281.
39. (a) Zeng, X.; Hu, Q.; Qian, M.; Negishi, E. J. Am. Chem. Soc. 2003, 125, 13636.
40. (b) Zeng, X.; Qian, M.; Hu, Q.; Negishi, E. Angew. Chem. Int. Ed. 2004, 43, 2259.