Stannylative cycloaddition of enynes catalyzed by palladium-iminophosphine

Journal of the American Chemical Society

Volumn 126, Issue 48, 2004, Pages 15650-15651

  Nakao, Yoshiaki ^a   Hirata, Yasuhiro ^a   Ishihara, Shinjiro ^a   Oda, Shinichi ^a   Yukawa, Tomoya ^a   Shirakawa, Eiji ^a   Hiyama, Tamejiro ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

IMINOPHOSPHINE; PALLADIUM; PHOSPHINE DERIVATIVE; TIN; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL REACTION; CONJUGATION; CYCLOADDITION; ISOLATION PROCEDURE; REACTION ANALYSIS; SUBSTITUTION REACTION; SYNTHESIS;

EID: 10044289300     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja044429s     Document Type: Article

References (28)

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15. For thermal or Lewis acid-mediated intramolecular [4 + 2] cycloadditions of enynes with alkynes, see: (a) Danheiser, R. L.; Gould, A. E.; Fernández de la Pradilla, R.; Helgason, A. L. J. Org. Chem. 1994, 59, 5514-5515. (b) Burrell, R. C.; Daoust, K. J.; Bradley, A. Z.; DiRico, K. J.; Johnson, R. P. J. Am. Chem. Soc. 1996, 118, 4218-4219.
16. For thermal or Lewis acid-mediated intramolecular [4 + 2] cycloadditions of enynes with alkynes, see: (a) Danheiser, R. L.; Gould, A. E.; Fernández de la Pradilla, R.; Helgason, A. L. J. Org. Chem. 1994, 59, 5514-5515. (b) Burrell, R. C.; Daoust, K. J.; Bradley, A. Z.; DiRico, K. J.; Johnson, R. P. J. Am. Chem. Soc. 1996, 118, 4218-4219.
17. (a) Shirakawa, E.; Yoshida, H.; Kurahashi, T.; Nakao, Y.; Hiyama, T. J. Am. Chem. Soc. 1998, 120, 2975-2976.
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19. For an account of the carbostannylation, see: (c) Shirakawa, E.; Hiyama, T. Bull. Chem. Soc. Jpn. 2002, 75, 1435-1450.
20. H-Sn values, and protodestannylation. For details, see Supporting Information.
21. Under the reaction conditions, 4a and hexabutylstannoxane did not give 3a.
22. For detailed results, see Supporting Information.
23. 119Sn NMR) and increased that of 4a (25% by GC). Thus, the formation of 4a might be derived partially from hydrolysis of 3a and/or 12 (see ref 16).
24. 3 for the reaction of enynes 2b-f caused isomerization of the alkenyl moieties of 3b-f. For detailed results, see Supporting Information. Maleic anhydride might affect the rapid reductive elimination of Cp and allyl from Cp(allyl)Pd due presumably to its strong π-accepting character, generating active Pd(0)-1 effectively. For the acceleration of reductive elimination by maleic anhydride, see: Yamamoto, T.; Yamamoto, A.; Ikeda, S. J. Am. Chem. Soc. 1971, 93, 3350-3359.
25. For nonstannylative versions of the intermolecular cross-cycloadditions, see ref 5c,e and refs cited in 5g-i.
26. 119Sn NMR. Maleic anhydride is not essential in these cases.
27. Tsuda, T.; Hayashi, T.; Satomi, H.; Kawamoto, T.; Saegusa, T. J. Org. Chem. 1986, 51, 537-540.
28. 3Sn group to give a stannylated product 3. Analogous reactions of a strained allene intermediate with a chlorine radical or proton has been reported: Rodríguez, D.; Navarro-Vázquez, A.; Castedo, L.; Domínguez, D.; Saá, C. J. Org. Chem. 2003, 68, 1938-1946, and ref 6a.