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Volumn 130, Issue 2, 2008, Pages 763-773

Oxidative diamination of alkenes with ureas as nitrogen sources: Mechanistic pathways in the presence of a high oxidation state palladium catalyst

Author keywords

[No Author keywords available]

Indexed keywords

CATALYST ACTIVITY; NITROGEN; OXIDATION; PALLADIUM COMPOUNDS; UREA;

EID: 41449087573     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja075041a     Document Type: Article
Times cited : (269)

References (134)
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    • This incorrect assumption of a trans-aminopalladation was recently cited in related work on aminopalladation24,25 and diamination. 7b,14b The authors apologize for the resulting confusion
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    • In a stricter sense, the nitrogen sources in this and related work are amides and, in a more correct manner, one should refer to these reactions as amidopalladation. See reference 15 for a general discussion. For convenience, we continue to use the term aminopalladation throughout this text
    • In a stricter sense, the nitrogen sources in this and related work are amides and, in a more correct manner, one should refer to these reactions as amidopalladation. See reference 15 for a general discussion. For convenience, we continue to use the term aminopalladation throughout this text.
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    • a values of related compounds (in water): 5.16 for N-butyl, N′-tosyl urea [http://www.syrres.com/esc/physdemo.htm] and 3.70 for ethyl N-tosyl carbamate [Taylor, L. D.; Pluhar, M.; Rubin, L. E. J. Polym. Sci., B; Polym. Phys. 1967, 5, 77].
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    • 42b The remaining coordination sites should be filled by additional donor groups L, which are unknown to date and might include solvent molecules, additional urea groups, acetic acid, acetate or halides (where present). The latter two would result in formation of formally anionic intermediates, which cannot be discarded completely at present.
    • 42b The remaining coordination sites should be filled by additional donor groups L, which are unknown to date and might include solvent molecules, additional urea groups, acetic acid, acetate or halides (where present). The latter two would result in formation of formally anionic intermediates, which cannot be discarded completely at present.
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    • While this manuscript was in the refereeing process, Goldberg described an identical mechanistic scenario for formation of achiral C-N bonds via reductive elimination from a methyl, tosylamido-Pt(IV) complex: Pawlikowski, A. V, Getty, A. D, Goldberg, K. I. J. Am. Chem. Soc. 2007, 129, 10382
    • While this manuscript was in the refereeing process, Goldberg described an identical mechanistic scenario for formation of achiral C-N bonds via reductive elimination from a methyl, tosylamido-Pt(IV) complex: Pawlikowski, A. V.; Getty, A. D.; Goldberg, K. I. J. Am. Chem. Soc. 2007, 129, 10382.
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    • Nicolaou introduced Burgess reagents for stoichiometric transformation of vicinal amino alcohols into cyclic sulfamides: (a) Nicolaou, K. C.; Longbottom, D. A.; Snyder, S. A.; Nalbanadian, A. Z.; Huang, X. Angew. Chem., Int. Ed. 2002, 41, 3866.
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    • For a recent cascade reaction with open relative stereochemistry in C-OAc bond formation from Pd(IV), see: Welbes, L. L.; Lyons, T. W.; Cychosz, K. A.; Sanford, M. S. J. Am. Chem. Soc. 2007, 129, 5836.
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