Stereo-and Regioselective Palladium-Catalyzed, 1,4-Acetoxychlorination of 1,3-Dienes. 1-Acetoxy-4-chloro-2-alkenes as Versatile Synthons in Organic Transformations

Journal of the American Chemical Society

Volumn 107, Issue 12, 1985, Pages 3676-3686

  Bäckvall, Jan E ^a   Nyström, Jan E ^a   Nordberg, Ruth E ^a  

^a ROYAL INSTITUTE OF TECHNOLOGY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001462910     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00298a043     Document Type: Article

References (49)

1. Balci, M. Chem. Rev. 1981, 81, 91. (b) Schenck, G. O.; Dunlop, D. E. Angew. Chem. 1956, 68, 248.
2. Kaneko, C.; Sugimoto, A.; Tanaka, S. Synthesis 1974, 876. (b) Gollnick, K.; Griesbeck, A. Tetrahedron Lett. 1983, 24, 3303.
3. Belleau, B.; Au-Young, Y. K. J. Am. Chem. Soc. 1963, 85, 64. (b) Krezse, G.; Dittel, W.; Melzer, H. Liebiqs Ann. Chem. 1981, 224 and references cited. (c) Keck, G. E.; Fleming, S. A. Tetrahedron Lett. 1978, 4763.
4. Streith, J.; Augelmann, G.; Fritz, H.; Strub, H. Tetrahedron Lett. 1982, 23, 1909. (b) Becker, Y.; Eisenstadt, A.; Shvo, Y. Tetrahedron 1978, 34, 801.
5. Neale, R. S. Synthesis 1971, 1. (b) Hassner, A.; Keogh, J. Tetrahedron Lett. 1975, 1575. (c) Truce, W. E.; Goralski, C. T.; Christensen, L. W.; Bavry, R. M. J. Org. Chem. 1970, 35, 4217. (d) Adams, D. R.; Bhatuagar, S. P.; Cookson, R. C. Tetrahedron Lett. 1974, 3197. (e) Matsumoto, H.; Nateaur, T.; Nikaido, T.; Nagai, Y. Chem. Lett. 1978, 115.
6. Bäckvall, J. E. Acc. Chem. Res. 1983, 16, 335.
7. Bäckvall, J. E.; Nordberg, R. E. J. Am. Chem. Soc. 1981, 103, 4959.
8. Bystrom, S. E.; Bäckvall, J. E.; Nordberg, R. E.; Nyström, J. E. Swedish Patent 8201 911–8, 1982.
9. Henry, P. M. “Palladium-Catalyzed Oxidation of Hydrocarbons”; D. Reidel: Dordrecht, 1980. (b) Henry, P. M. J. Org. Chem. 1974, 39, 3871; J. Am. Chem. Soc. 1972, 94, 7305. (c) Bäckvall, J. E. Tetrahedron Lett. 1977, 467.
10. For oxidation of nonconjugated dienes using the Pd11-CuCl2system in acetic acid, see: Heuman, A.; Waegell, B. Nouv. J. Chem. 1977, 1, 275. Heumann, A. Reglier, M., Waegell, B. Angew. Chem., Int. Ed. Engl. 1979, 18, 866, 867; Tetrahedron Lett. 1983, 24, 1971.
11. Nyström, J. E.; Bäckvall, J. E. J. Org. Chem. 1983, 48, 3947.
12. Trost, B. M. Acc. Chem. Res. 1980, 13, 385. (b) Tsuji, J. “Organic Synthesis with Palladium Compounds”; Springer-Verlag: Berlin, 1980. (c) Trost, B. M. Tetrahedron 1977, 33, 2615. (d) Trost, B. M.; Verhoeven, T. R. In “Comprehensive Organometallic Chemistry”; Wilkinson, G., Ed.; Pergamon Press: Oxford, 1982; Vol. 8, p 799.
13. Magid, R. M. Tetrahedron 1980, 36, 1901. (b) Yamamoto, Y.; Yamamoto, S.; Yatagai, H.; Maruyama, K. J. Am. Chem. Soc. 1980, 102, 2318. (c) Yamamoto, T.; Ishizu, J.; Yamamoto, A. J. Am. Chem. Soc 1981, 103, 6863. (d) Trost, B. M.; Lautens, M. J. Am. Chem. Soc 1981, 103, 5543. Roustan, J. L.; Marour, J. Y.; Houlihan, F. Tetrahedron Lett. 1979, 3721. (f) Goering, H. L.; Seitz, E. P.; Tseng, C. C. J. Org. Chem. 1981, 46, 5304.
14. Seebach, D.; Knochel, P. Helv. Chim. Acta 1984, 67, 261.
15. Tsuji, J.; Kataoka, H.; Kobayashi, Y. Tetrahedron Lett. 1981, 22, 2575. (b) Trost, B. M.; Molander, G. A. J. Am. Chem. Soc. 1981, 103, 5969. (c) Takahashi, T.; Kataoka, H.; Tsuji, J. J. Am. Chem. Soc. 1983, 105, 147.
16. Marino, J. P.; Floyd, D. M. Tetrahedron Lett. 1979, 675. (b) Marino, J. P.; Hatonaka, H. J. Org. Chem. 1979, 44, 4467. (c) Marino, J. P.; Abe, H. J. Am. Chem. Soc. 1981, 103, 2907. (d) Marino, J. P.; Jaen, J C. Tetrahedron Lett. 1983, 24, 441. (e) Anderson, R. J. J. Am. Chem. Soc. 1970, 92, 4978.
17. Bartlett, P. A. Tetrahedron 1980, 36, 2. (b) Tetrahedron 1984, 40, 2197–2343 (Symp. No. 16, T. Mukayama, Ed.). (c) Tetrahedron 1984, 40, 1213–1417 (Symp. No. 15, A. I. Meyers, Ed.). (d) Still, W. C.; Darst, K. P., J. Am. Chem. Soc. 1980, 102, 7387. (e) Fukuyama, T.; Vranesic, B.; Negri, D. P.; Kishi, Y. Tetrahedron Lett. 1978, 2741.
18. Bäckvall, J. E.; Byström, S. E.; Nyström, J. E. Tetrahedron, in press.
19. Wade, P. A.; Hinney, H. R.; Amin, N. W.; Vail, P. D.; Morrow, S. D.; Hardinger, S. A.; Saft, M. S. J. Org. Chem. 1981, 46, 765.
20. Olson, G. L.; Cheung, H. C.; Morgan, K. D.; Neukom, C.; Saucy, G. J. Org. Chem. 1976, 41, 3287.
21. Cainelli, G.; Cardillo, G. Acc. Chem. Res. 1981, 14, 89. (b) Julia, M.; Verpeux, J. N. Tetrahedron 1983, 39, 3289
22. Åkermark, B.; Nyström, J. E.; Rein, T.; Bäckvall, J. E.; Helquist, P.; Aslanian, R. Tetrahedron Lett. 1984, 25, 5719.
23. Genêt, J. P.; Balabane, M.; Bäckvall, J. E.; Nyström, J. E. Tetrahedron Lett. 1983, 24, 2745.
24. Nystrom, J. E.; Bäckvall, J. E., unpublished results.
25. Goldberg, R. N.; Hepler, L. G. Chem. Rev. 1968, 68, 229. (b) Aguilo, A. Adv. Organometal. Chem. 1967, 5, 327.
26. Although an ultraviolet study of PdCl2-LiCl solutions in anhydrous acetic acid (<0.02% water) indicated the presence of dimeric Li2Pd2Cl629bat low chloride concentration, our major species is most likely the monomeric complex for two reasons: (i) the concentration of LiCl is usually 40 times higher then the Pd(II) concentration; (ii) we are working in acetic acid containing 2% water (it is known that Pd(II) exists exclusively as PdCl42-in water above a chloride concentration of 0.1 M28). (b) Henry, P. M.; Marks, O. W. Inorg. Chem. 1971, 10, 373.
27. Henry, P. M.; Ward, G. A. J. Am. Chem. Soc. 1971, 93, 1494. (b) Andell, O. S.; Bäckvall, J. E. J. Organomet. Chem. 1983, 244, 401.
28. Donati, F.; Conti, F. Tetrahedron Lett. 1966, 1219.
29. 5Cl): Lukas, J.; Kramer, P. A. J. Organomet. Chem. 1971, 31, 111.
30. Semmelhack, M. F.; Le, H. T. M. J. Am. Chem. Soc. 1984, 106, 2715.
31. Bäckvall, J. E.; Björkman, E. E. J. Chem. Soc., Chem. Commun. 1982, 693. (b) Bäckvall, J. E.; Björkman, E. E.; Petterson, L.; Siegbahn, P. J. Am. Chem. Soc. 1984, 106, 4369.
32. Satsko, N. G.; Below, A. P.; Moiseev, I.I. Kinet. Catal. 1972, 13, 892; Chem. Abstr. 1973, 78, 83584c.
33. Hiramatsu, M.; Nakano, H.; Fujinami, T.; Sakai, S. J. Organomet. Chem. 1982, 236, 131. Hiramatsu, M.; Shiozaki, K.; Fujinami, T.; Sakai, S. J. Am. Chem. Soc 1983, 246, 303. (b) Chetcuti, M. J.; Howard, J. A. K.; Pfeffer, M.; Spencer, J. L.; Stone, F. G. A. J. Chem. Soc., Dalton Trans. 1981, 276. Chetcuti, M. J.; Herbert, J. A.; Howard, J. A. K. Pfeffer, M.; Spencer, J. L.; Stone, F. G. A.; Woodward, P. J. Am. Chem. Soc 1981, 284. (c) Uhlig, E.; Fischer, R.; Kirmse, R. J. Organomet. Chem. 1982, 239, 385.
34. Rowe, J. M.; White, D. A. J. Chem. Soc. A 1967, 1451. (b) Levanda, O. G.; Pek, G. I.; Moiseev, I. I. Zh. Org. Khim. 1971, 7, 217.
35. 3-alkenyl)palladium complexes related to 26 are well-known: Robinson, S. D.; Shaw, B. L. J. Chem. Soc. 1963, 4806. (b) Åkermark, B.; Bäckvall, J. E.; Löwenborg, A.; Zetterberg, K. J. Organomet. Chem. 1979, 166, C33.
36. Halpern, J.; Jewsbury, R. A. J. Organomet. Chem. 1979, 181, 223.
37. Trost, B. M.; Verhoeven, T. R.; Fortunak, J. M. Tetrahedron Lett. 1979, 2301. (b) Trost, B. M.; Verhoeven, T. R. J. Am. Chem. Soc. 1980, 102, 4730.
38. Bäckvall, J. E.; Nördberg, R. E.; Björkman, E. E.; Moberg, C. J. Chem. Soc., Chem. Commun. 1980, 943.
39. Nordberg, R. E.; Bäckvall, J. E. J. Organomet. Chem., in press.
40. Lukas, J.; van Leeuwen, P. W. N. M.; Volger, H. C.; Kouwenhoven, A. P. J. Organomet. Chem. 1973, 47, 153.
41. Hayashi, T.; Hagihara, T.; Konishi, M.; Kumada, M. J. Am. Chem. Soc. 1983, 105, 7767. (b) Hayashi, T.; Konishi, M.; Kumada, M. J. Chem. Soc., Chem. Commun. 1984, 107. (c) J. Am. Chem. Soc 1983, 736.
42. 7b, 46b(b) Faller, J. W.; Thomsen, M. E.; Mattina, M. J. J. Am. Chem. Soc. 1971, 93, 2642.
43. Tanigawa, Y.; Nishimura, K.; Kawasaki, A.; Murahashi, S. I. Tetrahedron Lett. 1982, 23, 5549.
44. Valpey, R. S.; Miller, D. J.; Estes, J. M.; Godleski, S. A. J. Org. Chem. 1982, 47, 4717.
45. Genêt, J. P.; Piau, F. J. Org. Chem. 1981, 46, 2414.
46. Reich, H. J.; Wollowitz, S. J. Am. Chem. Soc. 1982, 104, 7051.
47. Zelinski, N.; Gorsky, A. Chem. Ber. 1908, 41, 2630.
48. Schuster, D. J.; Palmer, J. M.; Dickerson, S. C. J. Org. Chem. 1966, 31, 4281.
49. The 60 MHz-spectra of 3 and 34 have been published but the shifts differ slightly from ours. (b) Ganem, B.; Small, V. R., Jr. J. Org. Chem. 1974, 39, 3728.