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Volumn 128, Issue 17, 2006, Pages 5818-5827

Dramatic acceleration of the Pd-catalyzed [4+2] benzannulation reaction of enynes and diynes in the presence of Lewis acids and bases: Expanded scope and new mechanistic insights

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE; DEUTERIUM; ISOMERIZATION; PALLADIUM; RATE CONSTANTS; REACTION KINETICS;

EID: 33646589622     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja060085p     Document Type: Article
Times cited : (72)

References (54)
  • 21
    • 0347812067 scopus 로고    scopus 로고
    • Palladium-catalyzed benzannulation reactions of conjugated enynes and diynes
    • Negishi, E., de Meijere, A., Eds.; Wiley: New York
    • (c) Saito, S.; Yamamoto, Y. Palladium-Catalyzed Benzannulation Reactions of Conjugated Enynes and Diynes. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., de Meijere, A., Eds.; Wiley: New York, 2002.
    • (2002) Handbook of Organopalladium Chemistry for Organic Synthesis
    • Saito, S.1    Yamamoto, Y.2
  • 28
    • 33646553404 scopus 로고    scopus 로고
    • note
    • As it was shown before, trisubstituted Z-enynes reacted much faster than their E-isomers, see ref 14.
  • 29
    • 33646598469 scopus 로고    scopus 로고
    • note
    • 12
  • 30
    • 33646541764 scopus 로고    scopus 로고
    • note
    • A slight excess of donor and acceptor alkynes (1.2 equiv) was used.
  • 31
    • 33646564153 scopus 로고    scopus 로고
    • note
    • tert-Butylacetylene was added as "dummy" alkyne to assist the reduction of Pd(II) to Pd(0).
  • 32
    • 33646547703 scopus 로고    scopus 로고
    • Transition metal-catalyzed synthesis of allenes
    • Krause, N., Hashmi, A. S. K., Eds.; Wiley-VCH Verlag GmbH & Co. KGaA: Weinheim, Germany
    • Ogasawara, M.; Hayashi, T. Transition Metal-Catalyzed Synthesis of Allenes. In Modern Allene Chemistry; Krause, N., Hashmi, A. S. K., Eds.; Wiley-VCH Verlag GmbH & Co. KGaA: Weinheim, Germany, 2004.
    • (2004) Modern Allene Chemistry
    • Ogasawara, M.1    Hayashi, T.2
  • 37
    • 33745402207 scopus 로고
    • For the discussion on the mechanism of the transition metal-catalyzed [2+2+2] trimerization reaction, see: (c) Schore, N. E. Chem. Rev. 1988, 88, 1081.
    • (1988) Chem. Rev. , vol.88 , pp. 1081
    • Schore, N.E.1
  • 42
    • 33646546788 scopus 로고
    • For allylic prototropic rearrangements catalyzed by Lewis acid, see: Cameron, G. S.; Stimson, V. R. Aust. J. Chem. 1977, 30, 923.
    • (1977) Aust. J. Chem. , vol.30 , pp. 923
    • Cameron, G.S.1    Stimson, V.R.2
  • 43
    • 33646584936 scopus 로고    scopus 로고
    • note
    • Analogously, partial incorporation of electrophilic entities into the benzene ring was observed in various types of benzannulation reactions. See ref 2b, 3a, 20.
  • 44
    • 33646569731 scopus 로고    scopus 로고
    • note
    • Geometry optimization was performed employing B3LYP in LANL2DZ basis. See Supporting Information for details.
  • 45
    • 33646575058 scopus 로고    scopus 로고
    • note
    • 3) revealed that the former complex is 1.7 kcal/mol more stable than the latter. This relatively insignificant difference does not allow for unambiguous assign-ment of either form 11a or 11b to the intermediate 11, which most likely exists in equilibrium between these two forms, which is affected by the temperature and effective concentration of phosphine ligands in the reaction mixture.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.