메뉴 건너뛰기




Volumn 132, Issue 37, 2010, Pages 12862-12864

Pd-catalyzed intermolecular ortho-C-H amidation of anilides by N-nosyloxycarbamate

Author keywords

[No Author keywords available]

Indexed keywords

AMIDATION; AMIDATION REACTION; ANILIDES; ARYLPALLADIUM COMPLEXES; CYCLOPALLADATION; FUNCTIONALIZATIONS; NITRENES; RATE LIMITING;

EID: 77956620860     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja106364r     Document Type: Article
Times cited : (313)

References (71)
  • 5
    • 77956641883 scopus 로고    scopus 로고
    • Drug Top. 2009, 6, 7. For information of the drugs see
    • Drug Top. 2009, 6, 7. For information of the drugs see: http://www.chem.cornell.edu/jn96/outreach.html.
  • 33
    • 70449558127 scopus 로고    scopus 로고
    • A recent example of Ag-catalyzed C-H amination was also reported
    • A recent example of Ag-catalyzed C-H amination was also reported: Cho, S. H., Kim, J. Y., Lee, S. Y., and Chang, S. Angew. Chem., Int. Ed. 2009, 48, 9127
    • (2009) Angew. Chem., Int. Ed. , vol.48 , pp. 9127
    • Cho, S.H.1    Kim, J.Y.2    Lee, S.Y.3    Chang, S.4
  • 39
    • 74949120125 scopus 로고    scopus 로고
    • For selected examples of Pd-catalyzed ortho-C-H bond functionalizations of anilides and arylureas, see Giri, R., Lam, J. K., and Yu, J.-Q. J. Am. Chem. Soc. 2010, 132, 686
    • (2010) J. Am. Chem. Soc. , vol.132 , pp. 686
    • Giri, R.1    Lam, J.K.2    Yu, J.-Q.3
  • 49
    • 77955797760 scopus 로고    scopus 로고
    • A recent example of Rh-catalyzed ortho-C-H bond vinylation of simple anilides was also reported
    • A recent example of Rh-catalyzed ortho-C-H bond vinylation of simple anilides was also reported: Patureaum, F. W. and Glorius, F. J. Am. Chem. Soc. 2010, 132, 9982
    • (2010) J. Am. Chem. Soc. , vol.132 , pp. 9982
    • Patureaum, F.W.1    Glorius, F.2
  • 55
    • 77956638190 scopus 로고    scopus 로고
    • note
    • Since both of the carbamate groups in the monoamidated products should be able to direct further amidation to the arene ring, formation of diamidation products should be possible. However, we did not observe formation of any diamidation products under our experimental conditions. Probably, the monoamidated products are less reactive for further palladation than the substrate anilides. Moreover, employing only 1.2 equiv of the N-nosyloxycarbamate would limit the chance for diamidation reactions.
  • 56
    • 70349934422 scopus 로고    scopus 로고
    • D) values of 2-5 have been reported for Pd-catalyzed ortho-C-H activation of arenes. For selected examples, see Stowers, K. J. and Sanford, M. S. Org. Lett. 2009, 11, 4584
    • (2009) Org. Lett. , vol.11 , pp. 4584
    • Stowers, K.J.1    Sanford, M.S.2
  • 58
    • 77956633987 scopus 로고    scopus 로고
    • For the synthesis of 1a-Pd, see Supporting Information for experimental details
    • For the synthesis of 1a-Pd, see Supporting Information for experimental details.
  • 59
    • 72249115788 scopus 로고    scopus 로고
    • Sanford and Ritter also observed a similar dependence on the exogenous free ligand for the stoichiometric C-H functionalizations; see Powers, D. C., Geibel, M. A. L., Klein, J. E. M. N., and Ritter, T. J. Am. Chem. Soc. 2009, 131, 17050
    • (2009) J. Am. Chem. Soc. , vol.131 , pp. 17050
    • Powers, D.C.1    Geibel, M.A.L.2    Klein, J.E.M.N.3    Ritter, T.4
  • 61
    • 77956644949 scopus 로고    scopus 로고
    • Ascorbic acid was found to suppress the amidation reaction in a dose-dependent manner; see Supporting Information for details. Yet, ascorbic acid may affect the catalytic turnovers by its reducing properties
    • Ascorbic acid was found to suppress the amidation reaction in a dose-dependent manner; see Supporting Information for details. Yet, ascorbic acid may affect the catalytic turnovers by its reducing properties.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.