Highly efficient synthesis of 1,1-difluoro-2-substituted-1,3-dienes and dienynes from gem-difluorohomoallenyl bromide via palladium-catalyzed cross-coupling reactions

Organic Letters

Volumn 3, Issue 14, 2001, Pages 2213-2215

  Shen, Qilong ^a   Hammond, Gerald B ^a  

^a UNIVERSITY OF MASSACHUSETTS DARTMOUTH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE;

EID: 0000455090     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0160654     Document Type: Article

References (39)

1. Schlosser, M. Angew. Chem., Int. Ed. 1998, 37, 1496-1513. Hudlicky, M.; Pavlath, A. E. Chemistry of Organic Fluorine Compounds II; American Chemical Society: Washington, DC, 1995.
2. Schlosser, M. Angew. Chem., Int. Ed. 1998, 37, 1496-1513. Hudlicky, M.; Pavlath, A. E. Chemistry of Organic Fluorine Compounds II; American Chemical Society: Washington, DC, 1995.
3. For leading references see: O'Hagan, D.; Rzepa, H. S. J. Chem. Soc. Chem. Commun. 1997, 645-652.
4. Biomedical Frontiers of Fluorine Chemistry; Ojima, I., McCarthy, J. R., Welch, J. T., Eds.; American Chemical Society: Washington, DC, 1996; Vol. 639.
5. Tozer, M. J.; Herpin, T. F. Tetrahedron 1996, 52, 8619-8683. Some recent leading references include: Yamazaki, T.; Hiraoka, S.; Sakamoto, J.; Kitazume, T. Org. Lett. 2001, 3, 743-746. Zhang, X.; Burton, D. J. Tetrahedron Lett. 2000, 41, 7791-7794. Huang, X.; He, P.; Shi, G. J. Org. Chem. 2000, 65, 627-629. Broadhurst, M. J.; Brown, S. J.; Percy, J. M.; Prime, M. E. J. Chem. Soc., Perkin Trans. 1 2000, 3217-3226.
6. Tozer, M. J.; Herpin, T. F. Tetrahedron 1996, 52, 8619-8683. Some recent leading references include: Yamazaki, T.; Hiraoka, S.; Sakamoto, J.; Kitazume, T. Org. Lett. 2001, 3, 743-746. Zhang, X.; Burton, D. J. Tetrahedron Lett. 2000, 41, 7791-7794. Huang, X.; He, P.; Shi, G. J. Org. Chem. 2000, 65, 627-629. Broadhurst, M. J.; Brown, S. J.; Percy, J. M.; Prime, M. E. J. Chem. Soc., Perkin Trans. 1 2000, 3217-3226.
7. Tozer, M. J.; Herpin, T. F. Tetrahedron 1996, 52, 8619-8683. Some recent leading references include: Yamazaki, T.; Hiraoka, S.; Sakamoto, J.; Kitazume, T. Org. Lett. 2001, 3, 743-746. Zhang, X.; Burton, D. J. Tetrahedron Lett. 2000, 41, 7791-7794. Huang, X.; He, P.; Shi, G. J. Org. Chem. 2000, 65, 627-629. Broadhurst, M. J.; Brown, S. J.; Percy, J. M.; Prime, M. E. J. Chem. Soc., Perkin Trans. 1 2000, 3217-3226.
8. Tozer, M. J.; Herpin, T. F. Tetrahedron 1996, 52, 8619-8683. Some recent leading references include: Yamazaki, T.; Hiraoka, S.; Sakamoto, J.; Kitazume, T. Org. Lett. 2001, 3, 743-746. Zhang, X.; Burton, D. J. Tetrahedron Lett. 2000, 41, 7791-7794. Huang, X.; He, P.; Shi, G. J. Org. Chem. 2000, 65, 627-629. Broadhurst, M. J.; Brown, S. J.; Percy, J. M.; Prime, M. E. J. Chem. Soc., Perkin Trans. 1 2000, 3217-3226.
9. Tozer, M. J.; Herpin, T. F. Tetrahedron 1996, 52, 8619-8683. Some recent leading references include: Yamazaki, T.; Hiraoka, S.; Sakamoto, J.; Kitazume, T. Org. Lett. 2001, 3, 743-746. Zhang, X.; Burton, D. J. Tetrahedron Lett. 2000, 41, 7791-7794. Huang, X.; He, P.; Shi, G. J. Org. Chem. 2000, 65, 627-629. Broadhurst, M. J.; Brown, S. J.; Percy, J. M.; Prime, M. E. J. Chem. Soc., Perkin Trans. 1 2000, 3217-3226.
10. Harrington, P. E.; Li, L.; Tius, M. A. J. Org. Chem. 1999, 64, 4025-4029.
11. Zapata, A.; Gu, Y.; Hammond, G. B. J. Org. Chem. 2000, 65, 227-234. Lan, Y.; Hammond, G. B. J. Org. Chem. 2000, 65, 4217-4221. Wang, Z.; Hammond, G. B. J. Chem. Soc., Chem. Commun. 1999, 2545-2546 and references therein.
12. Zapata, A.; Gu, Y.; Hammond, G. B. J. Org. Chem. 2000, 65, 227-234. Lan, Y.; Hammond, G. B. J. Org. Chem. 2000, 65, 4217-4221. Wang, Z.; Hammond, G. B. J. Chem. Soc., Chem. Commun. 1999, 2545-2546 and references therein.
13. Zapata, A.; Gu, Y.; Hammond, G. B. J. Org. Chem. 2000, 65, 227-234. Lan, Y.; Hammond, G. B. J. Org. Chem. 2000, 65, 4217-4221. Wang, Z.; Hammond, G. B. J. Chem. Soc., Chem. Commun. 1999, 2545-2546 and references therein.
14. Selected reviews, since 1999, include: Molander, G. A. Pure Appl. Chem. 2000, 72, 1757-1761. Houpis, J. N.; Lee, J. Tetrahedron 2000, 56, 817-846. Brummond, K. M. Adv. Cycloaddit. 1999, 6, 211-237. Larock, R. C. J. Organomet. Chem. 1999, 576, 111-124. Gevorgyan, V.; Yamamoto, Y. J. Organomet. Chem. 1999, 576, 232-247. Aggarwal, V. K.; Ali, A.; Coogan, M. P. Tetrahedron 1999, 55, 293-312. Sato, F.; Urabe, H.; Okamoto, S. Pure Appl. Chem. 1999, 71, 1511-1519.
15. Selected reviews, since 1999, include: Molander, G. A. Pure Appl. Chem. 2000, 72, 1757-1761. Houpis, J. N.; Lee, J. Tetrahedron 2000, 56, 817-846. Brummond, K. M. Adv. Cycloaddit. 1999, 6, 211-237. Larock, R. C. J. Organomet. Chem. 1999, 576, 111-124. Gevorgyan, V.; Yamamoto, Y. J. Organomet. Chem. 1999, 576, 232-247. Aggarwal, V. K.; Ali, A.; Coogan, M. P. Tetrahedron 1999, 55, 293-312. Sato, F.; Urabe, H.; Okamoto, S. Pure Appl. Chem. 1999, 71, 1511-1519.
16. Selected reviews, since 1999, include: Molander, G. A. Pure Appl. Chem. 2000, 72, 1757-1761. Houpis, J. N.; Lee, J. Tetrahedron 2000, 56, 817-846. Brummond, K. M. Adv. Cycloaddit. 1999, 6, 211-237. Larock, R. C. J. Organomet. Chem. 1999, 576, 111-124. Gevorgyan, V.; Yamamoto, Y. J. Organomet. Chem. 1999, 576, 232-247. Aggarwal, V. K.; Ali, A.; Coogan, M. P. Tetrahedron 1999, 55, 293-312. Sato, F.; Urabe, H.; Okamoto, S. Pure Appl. Chem. 1999, 71, 1511-1519.
17. Selected reviews, since 1999, include: Molander, G. A. Pure Appl. Chem. 2000, 72, 1757-1761. Houpis, J. N.; Lee, J. Tetrahedron 2000, 56, 817-846. Brummond, K. M. Adv. Cycloaddit. 1999, 6, 211-237. Larock, R. C. J. Organomet. Chem. 1999, 576, 111-124. Gevorgyan, V.; Yamamoto, Y. J. Organomet. Chem. 1999, 576, 232-247. Aggarwal, V. K.; Ali, A.; Coogan, M. P. Tetrahedron 1999, 55, 293-312. Sato, F.; Urabe, H.; Okamoto, S. Pure Appl. Chem. 1999, 71, 1511-1519.
18. Selected reviews, since 1999, include: Molander, G. A. Pure Appl. Chem. 2000, 72, 1757-1761. Houpis, J. N.; Lee, J. Tetrahedron 2000, 56, 817-846. Brummond, K. M. Adv. Cycloaddit. 1999, 6, 211-237. Larock, R. C. J. Organomet. Chem. 1999, 576, 111-124. Gevorgyan, V.; Yamamoto, Y. J. Organomet. Chem. 1999, 576, 232-247. Aggarwal, V. K.; Ali, A.; Coogan, M. P. Tetrahedron 1999, 55, 293-312. Sato, F.; Urabe, H.; Okamoto, S. Pure Appl. Chem. 1999, 71, 1511-1519.
19. Selected reviews, since 1999, include: Molander, G. A. Pure Appl. Chem. 2000, 72, 1757-1761. Houpis, J. N.; Lee, J. Tetrahedron 2000, 56, 817-846. Brummond, K. M. Adv. Cycloaddit. 1999, 6, 211-237. Larock, R. C. J. Organomet. Chem. 1999, 576, 111-124. Gevorgyan, V.; Yamamoto, Y. J. Organomet. Chem. 1999, 576, 232-247. Aggarwal, V. K.; Ali, A.; Coogan, M. P. Tetrahedron 1999, 55, 293-312. Sato, F.; Urabe, H.; Okamoto, S. Pure Appl. Chem. 1999, 71, 1511-1519.
20. Selected reviews, since 1999, include: Molander, G. A. Pure Appl. Chem. 2000, 72, 1757-1761. Houpis, J. N.; Lee, J. Tetrahedron 2000, 56, 817-846. Brummond, K. M. Adv. Cycloaddit. 1999, 6, 211-237. Larock, R. C. J. Organomet. Chem. 1999, 576, 111-124. Gevorgyan, V.; Yamamoto, Y. J. Organomet. Chem. 1999, 576, 232-247. Aggarwal, V. K.; Ali, A.; Coogan, M. P. Tetrahedron 1999, 55, 293-312. Sato, F.; Urabe, H.; Okamoto, S. Pure Appl. Chem. 1999, 71, 1511-1519.
21. 3 olefins ( Begue, J. P.; Bonnet-Delpon, D.; Bouvet, D.; Rock, M. H. J. Org. Chem. 1996, 61, 9111-9114. Hanzawa, Y.; Ishizawa, S.; Kobayashi, Y.; Taguchi, T. Chem. Pharm. Bull. 1990, 38, 1104-1106.).
22. 3 olefins ( Begue, J. P.; Bonnet-Delpon, D.; Bouvet, D.; Rock, M. H. J. Org. Chem. 1996, 61, 9111-9114. Hanzawa, Y.; Ishizawa, S.; Kobayashi, Y.; Taguchi, T. Chem. Pharm. Bull. 1990, 38, 1104-1106.).
23. 3 olefins ( Begue, J. P.; Bonnet-Delpon, D.; Bouvet, D.; Rock, M. H. J. Org. Chem. 1996, 61, 9111-9114. Hanzawa, Y.; Ishizawa, S.; Kobayashi, Y.; Taguchi, T. Chem. Pharm. Bull. 1990, 38, 1104-1106.).
24. This is in stark contrast to the diverse syntheses of terminal gemdifluoroolefins: Percy, J. M. Top. Curr. Chem. 1997, 193, 131-195.
25. The synthesis of 2-O-subsbstituted dienes from difluoroenol carbamate has been reported recently by DeBoos, G. A.; Fullbrook, J. J.; Owton, M. W.; Percy, J. M.; Thomas, A. C. Synlett. 2000, 963-966.
26. Ichikawa, J.; Ikeura, C.; Minami, T. Synlett 1992, 739-740.
27. Dolbier, J. W. R.; Burkholder, C. R.; Winchester, W. R. J. Org. Chem. 1984, 49, 1518-1522.
28. Wang, Z.; Hammond, G. B. J. Org. Chem. 2000, 65, 6547-6552.
29. Zimmer, R.; Dinesh, C. U.; Nandanan, E.; Khan, F. A. Chem. Rev. 2000, 100, 3067-3125.
30. For a review of coupling of fluorinated vinyl zinc reagents see: (a) Burton, D. J.; Lu, L. Top. Curr. Chem. 1997, 193, 45-89. (b) Burton, D. J.; Yang, Z. Y.; Morken, D. A. Tetrahedron 1994, 2993-3063.
31. For a review of coupling of fluorinated vinyl zinc reagents see: (a) Burton, D. J.; Lu, L. Top. Curr. Chem. 1997, 193, 45-89. (b) Burton, D. J.; Yang, Z. Y.; Morken, D. A. Tetrahedron 1994, 2993-3063.
32. Trost, B. M.; Tour, J. M. J. Org. Chem. 1989, 54, 484-486.
33. (16) At room temperature, in the presence of an aliphatic amine, 2a, undergoes a facile 5-endo-trig cyclization to give 2,2-difluoro-4-TIPS-2,5-dihydrofuran in excellent yield (see ref 12).
34. Suzuki, A. In Metal-catalyzed Cross-coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH Verlag: Weinheim, 1998; p 49-98.
35. Shen, W.; Thomas, S. A. Org. Lett. 2000, 2, 2857-2860. Hundertmark, T.; Littke, A. F.; Buchwald, S. L.; Fu, G. C. Org. Lett. 2000, 2, 1729-1731. Thorand, S.; Krause, N. J. Org. Chem. 1998, 63, 8551-8553.
36. Shen, W.; Thomas, S. A. Org. Lett. 2000, 2, 2857-2860. Hundertmark, T.; Littke, A. F.; Buchwald, S. L.; Fu, G. C. Org. Lett. 2000, 2, 1729-1731. Thorand, S.; Krause, N. J. Org. Chem. 1998, 63, 8551-8553.
37. Shen, W.; Thomas, S. A. Org. Lett. 2000, 2, 2857-2860. Hundertmark, T.; Littke, A. F.; Buchwald, S. L.; Fu, G. C. Org. Lett. 2000, 2, 1729-1731. Thorand, S.; Krause, N. J. Org. Chem. 1998, 63, 8551-8553.
38. For recent examples of the Sonogashira reaction applied to the synthesis of other fluorinated enynes see: Qing, F.-L.; Gao, W.-Z.; Ying, J. J. Org. Chem. 2000, 65, 2003-2006. Jennings, M. P.; Cork, E. A.; Ramachandran, P. V. J. Org. Chem. 2000, 65, 8763-8766.
39. For recent examples of the Sonogashira reaction applied to the synthesis of other fluorinated enynes see: Qing, F.-L.; Gao, W.-Z.; Ying, J. J. Org. Chem. 2000, 65, 2003-2006. Jennings, M. P.; Cork, E. A.; Ramachandran, P. V. J. Org. Chem. 2000, 65, 8763-8766.