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Volumn 8, Issue 4, 2006, Pages 689-692

A one-pot synthesis and functionalization of polyynes

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EID: 33644748064     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0528888     Document Type: Article
Times cited : (40)

References (53)
  • 1
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    • Diederich, F., Stang, P. J., Tykwinski, R. R., Eds.; Wiley-VCH: Weinheim, Germany
    • Acetylene Chemistry: Chemistry, Biology, and Material Science; Diederich, F., Stang, P. J., Tykwinski, R. R., Eds.; Wiley-VCH: Weinheim, Germany, 2005.
    • (2005) Acetylene Chemistry: Chemistry, Biology, and Material Science
  • 6
    • 20544450502 scopus 로고    scopus 로고
    • de Meijere, A., Diederich, F., Eds.; Wiley-VCH: Weinheim, Germany
    • (c) Metal-Catalyzed Cross-Coupling Reactions, 2nd ed.; de Meijere, A., Diederich, F., Eds.; Wiley-VCH: Weinheim, Germany, 2004.
    • (2004) Metal-Catalyzed Cross-Coupling Reactions, 2nd Ed.
  • 8
    • 0004003407 scopus 로고
    • Elsevier: Amsterdam
    • According to Brandsma, "...it is difficult to obtain very pure 1,3-pentadiyne in a good yield using a safe isolation procedure." Brandsma, L. Preparative Acetylenic Chemistry, 2nd ed.; Elsevier: Amsterdam, 1988; p 45.
    • (1988) Preparative Acetylenic Chemistry, 2nd Ed. , pp. 45
    • Brandsma, L.1
  • 9
    • 4644275985 scopus 로고    scopus 로고
    • Knorr, R. Chem. Rev. 2004, 104, 3795-3849.
    • (2004) Chem. Rev. , vol.104 , pp. 3795-3849
    • Knorr, R.1
  • 15
    • 33644755153 scopus 로고    scopus 로고
    • note
    • The ketones 4a-c,e and dibromides 5b,c,e have been previously reported, others were synthesized by analogous routes. See Supporting Information for references as well as synthetic and spectroscopic details for all new compounds.
  • 16
    • 33644778294 scopus 로고    scopus 로고
    • note
    • The FBW rearrangement can be successfully accomplished in pure toluene, but product isolation is more difficult due to its higher boiling point. This is an issue in cases were the triyne product is not particularly stable to heating; a mixture of hexanes and toluene is procedurally the easiest.
  • 17
    • 33644757340 scopus 로고    scopus 로고
    • note
    • It is has not yet been established if deprotonation precedes the FBW rearrangement, or vice versa. Given the good yields of the reactions, however, the former seems more likely because the latter should lead to byproduct formation resulting from protonation of the carbenoid intermediate by the terminal acetylene.
  • 18
    • 84919123738 scopus 로고
    • and references therein
    • A protocol for in situ formation and derivatization of 1-amino-di- and triynes has been reported. See: (a) Faul, D.; Himbert, G. Chem. Ber. 1988, 121, 1367-1369 and references therein.
    • (1988) Chem. Ber. , vol.121 , pp. 1367-1369
    • Faul, D.1    Himbert, G.2
  • 20
    • 0001677885 scopus 로고
    • For diynes, protocols exist for in situ acetylide formation and trapping. To our knowledge, these routes have not been generalized for triyne synthesis. For examples, see: (a) Negishi, E.; Okukado, N.; Lovich, S. F.; Luo, F.-T. J. Org. Chem. 1984, 49, 2629-2632.
    • (1984) J. Org. Chem. , vol.49 , pp. 2629-2632
    • Negishi, E.1    Okukado, N.2    Lovich, S.F.3    Luo, F.-T.4
  • 32
    • 3242776187 scopus 로고    scopus 로고
    • and references therein
    • Otera and co-workers reported a double elimination method of β-substituted sulfones that addresses this problem. See: Ye, F.; Orita, A.; Yaruva, J.; Hamada, T.; Otera, J. Chem. Lett. 2004, 33, 528-529 and references therein.
    • (2004) Chem. Lett. , vol.33 , pp. 528-529
    • Ye, F.1    Orita, A.2    Yaruva, J.3    Hamada, T.4    Otera, J.5
  • 35
    • 33644761513 scopus 로고    scopus 로고
    • note
    • The use of toluene rather than hexanes allows for higher reflux temperatures in the subsequent Negishi reaction.
  • 40
    • 84986716703 scopus 로고
    • Palladium-catalyzed alkynylation of acyl halides with metal acetylides. For copper: (a) Tohda, Y.; Sonogashira, K.; Hagihara, N. Synthesis 1977, 777-778.
    • (1977) Synthesis , pp. 777-778
    • Tohda, Y.1    Sonogashira, K.2    Hagihara, N.3
  • 48
    • 1442324531 scopus 로고    scopus 로고
    • and references therein
    • Palladium-catalyzed alkynylation of acyl halides with terminal alkynes has also been reported. See: Alonso, D. A.; Nájera, C.; Pacheco, M. C. J. Org. Chem. 2004, 69, 1615-1619 and references therein.
    • (2004) J. Org. Chem. , vol.69 , pp. 1615-1619
    • Alonso, D.A.1    Nájera, C.2    Pacheco, M.C.3
  • 53
    • 0002269581 scopus 로고
    • Trimethylsilyldiynyl ketones are conveniently formed via a Friedel-Crafts reaction. See: Walton, D. R. M.; Waugh, F. J. Organomet. Chem. 1972, 37, 45-56.
    • (1972) J. Organomet. Chem. , vol.37 , pp. 45-56
    • Walton, D.R.M.1    Waugh, F.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.