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Volumn 16, Issue 26, 1997, Pages 5706-5715

Energetics and mechanism of alkylamine N-H bond cleavage by palladium hydroxides: N-H activation by unusual acid-base chemistry

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EID: 3743139535     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om970856l     Document Type: Article
Times cited : (67)

References (62)
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  • 9
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    • The following paper includes the N-H activation of benzylamine, but the other amines in this work are arylamines, see: Glueck, D. S.; Winslow, L. J.; Bergman, R. G. Organometallics 1991, 10, 1462-1479.
    • (1991) Organometallics , vol.10 , pp. 1462-1479
    • Glueck, D.S.1    Winslow, L.J.2    Bergman, R.G.3
  • 19
    • 0001687271 scopus 로고
    • Imine hydrogenation catalyzed by rhodium and iridium complexes would be expected to occur through an amide complex. However, mechanistic data is scarce. For a direct observation of imine insertion that produces an amide complex potentially similar to those in catalytic systems, see: Fryzuk, M. D.; Piers, W. E. Organometallics 1990, 9, 986-98.
    • (1990) Organometallics , vol.9 , pp. 986-998
    • Fryzuk, M.D.1    Piers, W.E.2
  • 20
    • 0000041989 scopus 로고
    • For a recent review, see: James, B. R. Chem. Ind. 1995, 62, 167-180.
    • (1995) Chem. Ind. , vol.62 , pp. 167-180
    • James, B.R.1
  • 39
    • 84918716484 scopus 로고
    • and references therein
    • Collum, D. B. Acc. Chem. Res. 1993, 26, 227-234 and references therein.
    • (1993) Acc. Chem. Res. , vol.26 , pp. 227-234
    • Collum, D.B.1
  • 41
    • 85033161570 scopus 로고    scopus 로고
    • note
    • We have modified the procedure for the synthesis of 1 as described in the Experimental Section.
  • 43
    • 0029975357 scopus 로고    scopus 로고
    • X-ray data for 3a was previously submitted as Supporting Information, see: Driver, M. S.; Hartwig, J. F. J. Am. Chem. Soc. 1996, 118, 4206-4207.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 4206-4207
    • Driver, M.S.1    Hartwig, J.F.2
  • 46
    • 85033175122 scopus 로고    scopus 로고
    • note
    • The concentrations of water and amine were calculated based on their known starting concentrations and the stoichiometry of the reaction depicted in eq 1.
  • 47
    • 85033159533 scopus 로고    scopus 로고
    • Figures S1-S5 are provided as Supporting Information
    • Figures S1-S5 are provided as Supporting Information.


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