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Volumn 130, Issue 38, 2008, Pages 12645-12647

Nickel-catalyzed asymmetric cross-couplings of racemic propargylic halides with arylzinc reagents

Author keywords

[No Author keywords available]

Indexed keywords

DIHYDROFOLATE REDUCTASE INHIBITOR; HALIDE; LITHIUM SALT; NICKEL; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; PYRIMIDINE; ZINC DERIVATIVE;

EID: 52449132069     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja805165y     Document Type: Article
Times cited : (180)

References (26)
  • 4
    • 33847301925 scopus 로고    scopus 로고
    • For examples of applications by others of Ni/pybox catalysts to cross-coupling reactions of alkyl electrophiles, see: (a) Gong, H, Sinisi, R, Gagne, M. R. J. Am. Chem. Soc. 2007, 129, 1908-1909
    • For examples of applications by others of Ni/pybox catalysts to cross-coupling reactions of alkyl electrophiles, see: (a) Gong, H.; Sinisi, R.; Gagne, M. R. J. Am. Chem. Soc. 2007, 129, 1908-1909.
  • 8
    • 13444263825 scopus 로고    scopus 로고
    • For reviews of cross-coupling reactions of alkyl electrophiles, see: a
    • For reviews of cross-coupling reactions of alkyl electrophiles, see: (a) Frisch, A. C.; Beller, M. Angew. Chem., Int. Ed. 2005, 44, 674-688.
    • (2005) Angew. Chem., Int. Ed , vol.44 , pp. 674-688
    • Frisch, A.C.1    Beller, M.2
  • 11
    • 52449083809 scopus 로고    scopus 로고
    • For two of the pioneering investigations of palladium- and nickel-catalyzed cross-couplings of unactivated alkyl electrophiles, see: (a) Ishiyama, T, Abe, S, Miyaura, N, Suzuki, A. Chem. Lett. 1992, 691-694
    • For two of the pioneering investigations of palladium- and nickel-catalyzed cross-couplings of unactivated alkyl electrophiles, see: (a) Ishiyama, T.; Abe, S.; Miyaura, N.; Suzuki, A. Chem. Lett. 1992, 691-694.
  • 15
    • 84891029339 scopus 로고    scopus 로고
    • For some leading references to the chemistry of alkynes, see: a, Diederich, F, Stang, P. J, Tykwinski, R. R, Eds, Wiley-VCH: New York
    • For some leading references to the chemistry of alkynes, see: (a) Acetylene Chemistry; Diederich, F., Stang, P. J., Tykwinski, R. R., Eds.; Wiley-VCH: New York, 2005.
    • (2005) Acetylene Chemistry
  • 17
    • 80055045239 scopus 로고    scopus 로고
    • For a review of the Negishi reaction, see: a, Rappoport, Z, Marek, I, Eds, Wiley: New York, Chapter 11
    • For a review of the Negishi reaction, see: (a) Negishi, E.-i.; Hu, Q.; Huang, Z.; Wang, G.; Yin, N. In The Chemistry of Organozinc Compounds; Rappoport, Z., Marek, I., Eds.; Wiley: New York, 2006; Chapter 11.
    • (2006) The Chemistry of Organozinc Compounds
    • Negishi, E.-I.1    Hu, Q.2    Huang, Z.3    Wang, G.4    Yin, N.5
  • 18
    • 52449123290 scopus 로고    scopus 로고
    • For nickel-catalyzed asymmetric cross-coupling reactions of alkyl electrophiles, we have generally found that the use of a slight excess of ligand, relative to nickel, leads to improved yield and/or ee
    • For nickel-catalyzed asymmetric cross-coupling reactions of alkyl electrophiles, we have generally found that the use of a slight excess of ligand, relative to nickel, leads to improved yield and/or ee.
  • 19
    • 52449118387 scopus 로고    scopus 로고
    • Better, but still unsatisfactory, results were obtained if the magnesium/lithium salts were removed prior to cross-coupling
    • Better, but still unsatisfactory, results were obtained if the magnesium/lithium salts were removed prior to cross-coupling.
  • 23
    • 52449099717 scopus 로고    scopus 로고
    • 2·glyme or pybox ligand 1, essentially none of the desired alkyne is formed.
    • 2·glyme or pybox ligand 1, essentially none of the desired alkyne is formed.
  • 24
    • 52449119513 scopus 로고    scopus 로고
    • Palladium-catalyzed cross-couplings of propargylic electrophiles with organometallic reagents typically furnish the allene, not the alkyne, as the major product. See: (a) Tsuji, J, Mandai, T. In Metal-Catalyzed Cross-Coupling Reactions; de Meijere, A, Diederich, F, Eds, Wiley-VCH: New York, 2004; Chapter 10;
    • Palladium-catalyzed cross-couplings of propargylic electrophiles with organometallic reagents typically furnish the allene, not the alkyne, as the major product. See: (a) Tsuji, J.; Mandai, T. In Metal-Catalyzed Cross-Coupling Reactions; de Meijere, A., Diederich, F., Eds.; Wiley-VCH: New York, 2004; Chapter 10;
  • 25
    • 4544245050 scopus 로고    scopus 로고
    • Ma, S. Eur. J. Org. Chem. 2004, 1175-1183. The regioselectivity of carbon-carbon bond formation for the corresponding nickel-catalyzed processes has not been thoroughly investigated. For all of the Negishi reaction catalyzed by Ni/1 that are reported herein, essentially none of the allene is formed (<5%), regardless of the choice of R.
    • Ma, S. Eur. J. Org. Chem. 2004, 1175-1183. The regioselectivity of carbon-carbon bond formation for the corresponding nickel-catalyzed processes has not been thoroughly investigated. For all of the Negishi reaction catalyzed by Ni/1 that are reported herein, essentially none of the allene is formed (<5%), regardless of the choice of R.


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