Synthesis of unsaturated organotrifluoroborates via Wittig and Horner-Wadsworth-Emmons olefination

Journal of Organic Chemistry

Volumn 71, Issue 16, 2006, Pages 6135-6140

  Molander, Gary A ^a   Figueroa, Ruth ^a  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

E-ISOMERS; HORNER-WADSWORTH-EMMONS OLEFINATION; ORGANOTRIFLUOROBORATES; Z-ISOMERS;

ISOMERS; OLEFINS; REACTION KINETICS; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

FLUORINE COMPOUNDS;

ORGANOMETALLIC COMPOUND; ORGANOTRIFLUOROBORATE DERIVATIVE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; HORNER REACTION; HORNER WADSWORTH EMMONS REACTION; ISOMERISM; MOLECULAR STABILITY; OLEFINATION; PRODUCT RECOVERY; REACTION ANALYSIS; REACTION OPTIMIZATION; STEREOCHEMISTRY; SUBSTITUTION REACTION; SYNTHESIS;

ALKENES; BORATES; FLUORINE; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; PHOSPHONIC ACIDS; POTASSIUM;

EID: 33746868950     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo060863w     Document Type: Article

References (50)

1. Brown, H. C.; Bhat, N. G.; Somayaji, V. Organometallics 1983, 2, 1311.
2. (a) Burgess, K.; Ohlmeyer, M. J. Chem. Rev. 1991, 91, 1179.
3. (b) Pereira, S.; Srebnik, M. J. Am. Chem. Soc. 1996, 118, 909.
4. (c) Kabalka, G. W.; Narayana, C.; Reddy, N. K. Synth. Commun. 1994, 24, 1019.
5. (d) Männig, D.; Nöth, H. Angew. Chem., Int. Ed. Engl. 1985, 24, 878.
6. (e) Evans, D. A.; Muci, A. R.; Stürmer, R. J. Org. Chem. 1996, 61, 3224.
7. Matteson, D. S. Tetrahedron 1989, 45, 1859.
8. Reviews: (a) Maryanoff, B. E.; Reitz, A. B. Chem. Rev. 1989, 89, 863.
9. (b) Vedejs, E.; Peterson, M. J. In Topics in Stereochemistry; Eliel, E. L., Wilen, S. H., Eds.; John Wiley & Sons: New York, 1994; Vol. 21, p 1.
10. (c) Vedejs, E.; Peterson, M. J. In Advances in Carbanion Chemistry; Snieckus, V., Ed.; JAI Press Inc.: New York, 1996; Vol. 2, pp 1-86.
11. (d) Edmonds, M.; Abell, A. In Modern Carbonyl Olefination Methods and Applications; Takeda, T., Ed.; Wiley-VCH: Weinheim, Germany, 2004; pp 1-17.
12. Walker, B. J. In Organophosphorus Reagents in Organic Synthesis; Gadogan, J. I. G., Ed.; Academic Press: London, UK, 1979; pp 155-205.
13. (a) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
14. (b) Suzuki, A. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, Germany, 1998; pp 49-97.
15. (c) Suzuki, A. J. Organomet. Chem. 1999, 576, 147.
16. Wittig: (a) Lautens, M.; Mancuso, J. J. Org. Chem. 2004, 69, 3478.
17. (b) Lautens, M.; Marquardt, T. J. Org. Chem. 2004, 69, 4607.
18. Wittig-Horner under Masamune conditions: (c) Kobayashi, Y.; Tokoro, Y.; Watatani, K. Tetrahedron Lett. 1998, 39, 7537.
19. (d) Kobayashi, Y.; Tokoro, Y.; Watatani, K. Eur. J. Org. Chem. 2000, 3825.
20. HWE or Horner-Emmons-Wittig: (a) Schmidt, U.; Leitenberger, V.; Griesser, H.; Schmidt, J.; Meyer, R. Synthesis 1992, 1248.
21. (b) Park, K. C.; Yoshino, K.; Tomiyasu, H. Synthesis 1999, 2041.
22. (c) Busnel, O.; Carreaux, F.; Carboni, B.; Pethe, S.; Goff, S. V.-L.; Mansuy, D.; Boucher, J.-L. Bioorg. Med. Chem. 2005, 13, 2373.
23. (d) Gopalarathnam, A.; Nelson, S. G. Org. Lett. 2006, 8, 7.
24. Reviews: (a) Darses, S.; Genêt, J.-P. Eur. J. Org. Chem. 2003, 4313.
25. (b) Molander, G. A.; Figueroa, R. Aldrichim. Acta 2005, 38, 49.
26. (a) Vedejs, E.; Chapman, R. W.; Fields, S. C.; Lin, S.; Schrimpf, M. R. J. Org. Chem. 1995, 60, 3020.
27. (b) Vedejs, E.; Fields, S. C.; Hayashi, R.; Hitchcock, S. R.; Powell, D. R.; Schrimpf, M. R. J. Am. Chem. Soc. 1999, 121, 2460.
28. (a) Batey, R. A.; Thadani, A. N. Org. Lett. 1999, 1, 1683.
29. (b) Pucheault, M.; Darses, S.; Genêt, J.-P. Eur. J. Org. Chem. 2002, 3552.
30. (c) Pucheault, M.; Darses, S.; Genêt, J.-P. Tetrahedron Lett. 2002, 43, 6155.
31. (d) Navarre, L.; Pucheault, M.; Darses, S.; Genêt, J.-P. Tetrahedron Lett. 2005, 46, 4247.
32. (a) Batey, R. A.; Thadani, A. N.; Smil, D. V. Tetrahedron Lett. 1999, 40, 4289.
33. (b) Batey, R. A.; Thadani, A. N.; Smil, D. V. Synthesis 2000, 990.
34. (c) Thadani, A. N.; Batey, R. A. Org. Lett. 2002, 4, 3827.
35. (d) Thadani, A. N.; Batey, R. A. Tetrahedron Lett. 2003, 44, 8051.
36. (e) Li, S.-W.; Batey, R. A. Chem. Commun. 2004, 12, 1382.
37. Molander, G. A.; Ribagorda, M. J. Am. Chem. Soc. 2003, 125, 11148.
38. Molander, G. A.; Figueroa, R. Org. Lett. 2006, 8, 75.
39. Bestmann, H. J.; Stransky, W.; Vostrowsky, O. Chem. Ber. 1976, 109, 1694.
40. Anderson, R. J.; Henrick, C. A. J. Am. Chem. Soc. 1975, 97, 4327.
41. Bressy, C.; Bruyère, D.; Bouyssi, D.; Balme, G. ARKIVOC 2002, 5, 127.
42. Vedejs, E.; Cabaj, J.; Peterson, M. J. J. Org. Chem. 1993, 58, 6509.
43. Molander, G. A.; Biolatto, B. J. Org. Chem. 2003, 68, 4302.
44. Kalinin, A. V.; Scherer, S.; Snieckus, V. Angew. Chem., Int. Ed. 2003, 42, 3399.
45. Maryanoff, B. E.; Reitz, A. B.; Duhl-Emscoiler, B. A. J. Am. Chem. Soc. 1985, 107, 217.
46. Prepared according to a procedure reported by: Mauduit, M.; Kouklovsky, C.; Langlois, Y. Tetrahedron Lett. 1998, 39, 6857.
47. Batey, R. A.; Quach, T. D. Tetrahedron Lett. 2001, 42, 9099.
48. The reaction begins heterogeneous and becomes homogeneous as it reaches 90 °C and remains homogeneous until completion.
49. Complete removal of DMF is required to facilitate isolation of the product. Slight heating (50 °C) can be used to facilitate DMF removal.
50. At this stage partial precipitation of the product was observed.