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Volumn 9, Issue 3, 2007, Pages 457-460

Mild conditions for the synthesis of functionalized pyrrolidines via Pd-catalyzed carboamination reactions

Author keywords

[No Author keywords available]

Indexed keywords

1,4-DIOXANE; ACETIC ACID DERIVATIVE; ALKENE; BROMINATED HYDROCARBON; CARBONIC ACID DERIVATIVE; CESIUM; DIOXANE; DIOXANE DERIVATIVE; ESTER; KETONE; MESYLIC ACID DERIVATIVE; NITRO DERIVATIVE; PALLADIUM; PYRROLIDINE DERIVATIVE; SOLVENT; TRIFLUOROMETHANESULFONIC ACID; UNCLASSIFIED DRUG;

EID: 33847074190     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol062808f     Document Type: Article
Times cited : (50)

References (27)
  • 1
    • 33747139387 scopus 로고    scopus 로고
    • For recent reviews, see: a
    • For recent reviews, see: (a) Bellina, F.; Rossi, R. Tetrahedron 2006, 62, 7213-7256.
    • (2006) Tetrahedron , vol.62 , pp. 7213-7256
    • Bellina, F.1    Rossi, R.2
  • 10
    • 33847032130 scopus 로고    scopus 로고
    • For a review on other Pd-catalyzed alkene carboamination reactions that afford pyrrolidine products, see: (a) Wolfe, J. P. Eur. J. Org. Chem. 2007, in press. See also:
    • For a review on other Pd-catalyzed alkene carboamination reactions that afford pyrrolidine products, see: (a) Wolfe, J. P. Eur. J. Org. Chem. 2007, in press. See also:
  • 15
    • 33847043530 scopus 로고    scopus 로고
    • Dpe-phos, bis(2-diphenylphosphinophenyl)ether
    • Dpe-phos = bis(2-diphenylphosphinophenyl)ether.
  • 16
    • 33847017281 scopus 로고    scopus 로고
    • 3 and other weak bases in Pd-catalyzed N-arylation reactions of amines with aryl halides has been reported. For reviews, see:
    • 3 and other weak bases in Pd-catalyzed N-arylation reactions of amines with aryl halides has been reported. For reviews, see:
  • 18
    • 0042291889 scopus 로고    scopus 로고
    • Astruc, D, Ed, Wiley-VCH: Weinheim
    • (b) Hartwig, J. F. In Modern Arene Chemistry; Astruc, D., Ed., Wiley-VCH: Weinheim, 2002; pp 107-168.
    • (2002) Modern Arene Chemistry , pp. 107-168
    • Hartwig, J.F.1
  • 20
    • 33847067502 scopus 로고    scopus 로고
    • 3N.
    • 3N.
  • 21
    • 33847076808 scopus 로고    scopus 로고
    • In some cases use of DME as solvent provided results comparable to those obtained with dioxane (Table 2, entries 3, 4, 6, and 8.)
    • In some cases use of DME as solvent provided results comparable to those obtained with dioxane (Table 2, entries 3, 4, 6, and 8.)
  • 22
    • 33645387715 scopus 로고    scopus 로고
    • 2 are not fully understood, but may result from coordination of dba (dibenzylideneacetone) to the metal at key stages in the catalytic cycle, or through the formation of dba-ligated complexes that lie outside of the catalytic cycle. Dba has previously been demonstrated to have a large impact on the rates of Pd-catalyzed or -mediated process. For lead references, see: (a) Shekhar, S.; Ryberg, P.; Hartwig, J. F.; Mathew, J. S.; Blackmond, D. G.; Strieter, E. R.; Buchwald, S. L. J. Am. Chem. Soc. 2006, 128, 3584-3591.
    • 2 are not fully understood, but may result from coordination of dba (dibenzylideneacetone) to the metal at key stages in the catalytic cycle, or through the formation of dba-ligated complexes that lie outside of the catalytic cycle. Dba has previously been demonstrated to have a large impact on the rates of Pd-catalyzed or -mediated process. For lead references, see: (a) Shekhar, S.; Ryberg, P.; Hartwig, J. F.; Mathew, J. S.; Blackmond, D. G.; Strieter, E. R.; Buchwald, S. L. J. Am. Chem. Soc. 2006, 128, 3584-3591.
  • 27
    • 33847071635 scopus 로고    scopus 로고
    • These conditions were also less effective for carboamination reactions of γ-(N-arylamino)alkenes; the desired N-arylpyrrolidine products were obtained in low to moderate yield (35-55%).
    • These conditions were also less effective for carboamination reactions of γ-(N-arylamino)alkenes; the desired N-arylpyrrolidine products were obtained in low to moderate yield (35-55%).


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