Palladium-Catalyzed Reactions of Acyl Chlorides with (1-Alkynyl)tributylstannanes. A Convenient Synthesis for 1-Alkynyl Ketones

Journal of Organic Chemistry

Volumn 47, Issue 13, 1982, Pages 2549-2553

  Logue, Marshall W ^a   Teng, Kelly ^a  

^a NORTH DAKOTA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001103972     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00134a010     Document Type: Article

References (41)

1. For recent reviews see: Fuks, R.; Viehe, H. G. In “Chemistry of Acetylenes”; Viehe, H. G., Ed.; Marcel Dekker: New York, 1969; Chapter 8.
2. Miller, S. I.; Tanaker, R. In “Selective Organic Transformations”; Thyagrajan, B. S., Ed.; Wiley-Interscience: New York, 1970; Vol. 1, Chapter 4.
3. Winterfeldt, E. In “Newer Methods of Preparative Organic Chemistry”; Foerst, W., Ed.; Verlag Chemie: Weinheim Bergstr., Germany, 1971; Vol VI, p 243.
4. George, M. V.; Kheton, S. K.; Gupta, R. K. Adv. Heterocycl. Chem. 1976, 19, 279.
5. Tam, S.Y.-K.; Klein, R. S.; de las Heras, F. G.; Fox, J. J. J. Org. Chem. 1979, 44, 4854 and references therein.
6. Gupta, C. M.; Jones, G. H.; Moffatt, J. G. J. Org. Chem. 1976, 41, 3000.
7. Buchanan, J. G.; Edgar, A. R.; Power, M. J.; Williams, G. C. Carbohydr. Res. 1977, 55, 225 and references therein.
8. Bowden, K.; Jones, E. R. H. J. Chem. Soc. 1964, 953.
9. Davis, R. B.; Scheiber, D. H. J. Am. Chem. Soc. 1956, 78, 1675.
10. Normant, J. F. Synthesis 1972, 63.
11. Logue, M. W.; Moore, G. L. J. Org. Chem. 1975, 40, 131.
12. Unpublished observations by M. W. Logue.
13. Birkofer, L.; Ritter, A.; Uhlenbrauck, H. Chem. Ber. 1963, 96, 3280.
14. Walton, D. R. M.; Waugh, F. J. Organomet. Chem. 1972, 37, 45.
15. Yashina, O. G.; Kaigorodova, T. D.; Zarva, T. V.; Vereshchagin, L. I. Zh. Org. Khim. 1968, 4, 1904.
16. Yashina, O. G.; Zarva, T. V.; Kaigorodova, T. D.; Vereshchagin, L. I. Zh. Org. Khim. 1968, 4, 2104.
17. Schmidt, U.; Schwochau, M. Chem. Ber. 1964, 97, 1649.
18. Tohda, Y.; Sonogashita, K.; Hagihara, N. Synthesis 1977, 777.
19. Neumann, W. P.; Kleiner, F. G. Justus Liebigs Ann. Chem. 1968, 716, 29.
20. 3COCl produces the alkynyl ketone in 83% yield.
21. Milstein, D.; Stille, J. K. J. Am. Chem. Soc. 1978, 100, 3636;
22. J. Org. Chem. 1979, 44, 1613.
23. Chem. Eng. News 1975, 53(17), 29.
24. Zapp, J. A. Science 1975, 190, 422.
25. Coulson, D. R. Inorg. Synth. 1972, 13, 121.
26. Lau, S. K. Y.; Wang, P. K.; Stille, J. K. J. Am. Chem. Soc. 1976, 98, 5832.
27. Fitton, P.; McKeon, J. E.; Ream, B. C. Chem. Commun. 1969, 370.
28. King, A. O.; Negishi, E.-I.; Vallani, F. J., Jr.; Silverira, A., Jr. J. Org. Chem. 1978, 43, 358.
29. Vollhardt, K. P. C. Ann. N. Y. Acad. Sci. 1980, 33, 241 and references therein.
30. Lensink, A. J.; Marsman, J. W.; Budding, H. H.; Noltes, J. G.; Van der Kerk, G. J. M. Recl. Trau. Chem. Pays-Bas 1965, 84, 567.
31. Corey, E. J.; Kim, C. U.; Chen, R. H.; Takeda, M. J. Am. Chem. Soc. 1972, 94, 4395.
32. Davis, A. G.; Kleinschmidt, D. C.; Palan, P. R.; Varishta, S. C. J. Chem. Soc. C 1971, 3972.
33. Neumann, W. P. “The Organic Chemisty of Tin”; Moser, W., Translator; Wiley-Interscience: London, 1970; p 58.
34. Sonogasjora, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 4467.
35. Fitton, P.; Johnson, M. P.; McKeon, J. E. J. Chem. Soc., Chem. Commun. 1968, 6.
36. Brandsma, L. “Preparative Acetylenic Chemistry”; Elsevier: Amsterdam, 1971; pp 118–119.
37. Corey, E. J.; Venkateswarlu, A. J. Am. Chem. Soc. 1972, 94, 6190.
38. Hartmann, H.; Reiss, W.; Karbstein, B. Naturwissenschaften 1959, 46, 321.
39. Nightingale, D.; Wadsworth, F. J. Am. Chem. Soc. 1945, 67, 416.
40. Tuerck, U.; Behringer, H. Chem. Ber. 1965, 98, 3020.
41. Fabritsy, A. Zh. Obshch. Khim. 1958, 28, 5227.