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Volumn 75, Issue 8, 2010, Pages 2756-2759

Use of aryl chlorides as electrophiles in Pd-catalyzed alkene difunctionalization reactions

Author keywords

[No Author keywords available]

Indexed keywords

ARYL CHLORIDE; DIFUNCTIONALIZATION; ELECTROPHILES; HETEROCYCLES; ISOXAZOLIDINES; N-ARYLATIONS; PYRROLIDINES; TETRAHYDROFURANS;

EID: 77950997306     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo100344k     Document Type: Article
Times cited : (34)

References (40)
  • 7
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    • For reviews on Pd-catalyzed carboamination reactions, see
    • For reviews on Pd-catalyzed carboamination reactions, see: Wolfe, J. P. Eur. J. Org. Chem. 2007, 571
    • (2007) Eur. J. Org. Chem. , pp. 571
    • Wolfe, J.P.1
  • 9
    • 44949263787 scopus 로고    scopus 로고
    • For related syntheses of imidazolidin-2-ones, isoxazolidines, pyrazolidines, piperazines, and morpholines via Pd-catalyzed carboamination reactions, see
    • For related syntheses of imidazolidin-2-ones, isoxazolidines, pyrazolidines, piperazines, and morpholines via Pd-catalyzed carboamination reactions, see: Fritz, J. A.; Wolfe, J. P. Tetrahedron 2008, 64, 6838
    • (2008) Tetrahedron , vol.64 , pp. 6838
    • Fritz, J.A.1    Wolfe, J.P.2
  • 16
    • 38349162901 scopus 로고    scopus 로고
    • For Cu- or Au-catalyzed carboamination reactions, see
    • For Cu- or Au-catalyzed carboamination reactions, see: Fuller, P. H.; Chemler, S. R. Org. Lett. 2007, 9, 5477
    • (2007) Org. Lett. , vol.9 , pp. 5477
    • Fuller, P.H.1    Chemler, S.R.2
  • 17
    • 35848934578 scopus 로고    scopus 로고
    • references cited therein
    • Zeng, W.; Chemler, S. R. J. Am. Chem. Soc. 2007, 129, 12948 and references cited therein.
    • (2007) J. Am. Chem. Soc. , vol.129 , pp. 12948
    • Zeng, W.1    Chemler, S.R.2
  • 19
    • 67650507268 scopus 로고    scopus 로고
    • For alkene carboamination reactions involving solvent C?H bond functionalization, see
    • For alkene carboamination reactions involving solvent C?H bond functionalization, see: Rosewall, C. F.; Sibbald, P. A.; Liskin, D. V.; Michael, F. E. J. Am. Chem. Soc. 2009, 131, 9488
    • (2009) J. Am. Chem. Soc. , vol.131 , pp. 9488
    • Rosewall, C.F.1    Sibbald, P.A.2    Liskin, D.V.3    Michael, F.E.4
  • 21
    • 70349934214 scopus 로고    scopus 로고
    • The use of aryl chlorides as electrophiles in Pd-catalyzed carboamination reactions that afford aziridines or pyrrolizidin-2-ones has recently been reported. See
    • The use of aryl chlorides as electrophiles in Pd-catalyzed carboamination reactions that afford aziridines or pyrrolizidin-2-ones has recently been reported. See: Hayashi, S.; Yorimitsu, H.; Oshima, K. Angew. Chem., Int. Ed. 2009, 48, 7224
    • (2009) Angew. Chem., Int. Ed. , vol.48 , pp. 7224
    • Hayashi, S.1    Yorimitsu, H.2    Oshima, K.3
  • 30
    • 77950964836 scopus 로고    scopus 로고
    • Note
    • 1H NMR suggests that mixtures of pyrrolidine regioisomers are formed, and competing substrate N -arylation also occurs. This outcome may be due to a combination of relatively slow aminopalladation of the more hindered internal alkene combined with relatively slow reductive elimination from a secondary alkylpalladium intermediate analogous to II.
  • 31
    • 77950976731 scopus 로고    scopus 로고
    • The installation of the aryl group at C5 rather than C6 in 2f ? g results from β-hydride elimination/hydridopalladation processes similar to those illustrated in Scheme 1 (II → IV → 3 ? 5). Selective formation of the 6-aryl isomers has been ascribed to the relative stabilities of intermediates along this pathway. For a detailed discussion of reaction mechanism and the origin of these products, see ref 1c
    • The installation of the aryl group at C5 rather than C6 in 2f ? g results from β-hydride elimination/hydridopalladation processes similar to those illustrated in Scheme 1 (II → IV → 3 ? 5). Selective formation of the 6-aryl isomers has been ascribed to the relative stabilities of intermediates along this pathway. For a detailed discussion of reaction mechanism and the origin of these products, see ref 1c.
  • 34
    • 77950965451 scopus 로고    scopus 로고
    • The reactivity of intermediates I and II is highly dependent on ligand structure. For further discussion, see refs 1c and 2a
    • The reactivity of intermediates I and II is highly dependent on ligand structure. For further discussion, see refs 1c and 2a.
  • 35
    • 77950974847 scopus 로고    scopus 로고
    • S-Phos = 2-dicyclohexylphosphino-2′,6′-dimethoxy-1,1′- biphenyl
    • S-Phos = 2-dicyclohexylphosphino-2′,6′-dimethoxy-1,1′- biphenyl.
  • 38
    • 0347653089 scopus 로고    scopus 로고
    • 1H NMR showed predominantly the desired product, with little or no evidence of side product formation. Modest yields obtained in some transformations may be due to base-mediated substrate decomposition. See
    • 1H NMR showed predominantly the desired product, with little or no evidence of side product formation. Modest yields obtained in some transformations may be due to base-mediated substrate decomposition. See: Tom, N. J.; Simon, W. M.; Frost, H. N.; Ewing, M. Tetrahedron Lett. 2004, 45, 905
    • (2004) Tetrahedron Lett. , vol.45 , pp. 905
    • Tom, N.J.1    Simon, W.M.2    Frost, H.N.3    Ewing, M.4
  • 39
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    • Note
    • 3 as ligand, see ref 3e. For transformations that generate trans -2,5-disubstituted tetrahydrofurans using bis(2-diphenylphosphinophenyl)ether (dpe-phos) as ligand, see: Hay, M. B.; Hardin, A. R.; Wolfe, J. P. J. Org. Chem. 2005, 70, 3099
    • (2005) J. Org. Chem. , vol.70 , pp. 3099
    • Hay, M.B.1    Hardin, A.R.2    Wolfe, J.P.3
  • 40
    • 77950968137 scopus 로고    scopus 로고
    • Efforts to employ a Boc-protected analogue of 13 also failed to provide a substituted morpholine product. Base-mediated decomposition of the substrate was observed
    • Efforts to employ a Boc-protected analogue of 13 also failed to provide a substituted morpholine product. Base-mediated decomposition of the substrate was observed.


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