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Volumn 125, Issue 46, 2003, Pages 13978-13980

Insights into the Origin of High Activity and Stability of Catalysts Derived from Bulky, Electron-Rich Monophosphinobiaryl Ligands in the Pd-Catalyzed C-N Bond Formation

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; NITROGEN; PALLADIUM; PHOSPHINE DERIVATIVE;

EID: 0242582867     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja037932y     Document Type: Article
Times cited : (245)

References (34)
  • 8
    • 33751386097 scopus 로고
    • For other mechanistic studies using aryl chlorides, see: (a) Portnoy, M. ; Milstein, D. Organometallics 1993, 12, 1665.
    • (1993) Organometallics , vol.12 , pp. 1665
    • Portnoy, M.1    Milstein, D.2
  • 18
    • 0242479003 scopus 로고    scopus 로고
    • note
    • Using ligands 1-5 the reaction in eq 1 went to >99% conversion and >98% yield.
  • 21
    • 0242479000 scopus 로고    scopus 로고
    • note
    • The intrinsic activity of ligand 1 is probably even greater than suggested by the data in Figure 1 because at the catalyst concentrations employed in this experiment its reaction rate approaches the limit of detection of the reaction calorimeter.
  • 22
    • 0242479001 scopus 로고    scopus 로고
    • note
    • Decreasing consecutive initial rates for reactions with successively lower initial [amine] suggests intrinsic positive order kinetics in [amine]; however, it could also be attributed to zero-order kinetics in [amine] and decreasing [catalyst] due to catalyst deactivation.
  • 23
    • 0242647365 scopus 로고    scopus 로고
    • note
    • 2Pd(II) complex as we propose here; see refs 4, 5, 6, and 9.
  • 24
    • 0012253713 scopus 로고    scopus 로고
    • A similar mechanism has been proposed for the Pd-catalyzed aerobic alcohol oxidation: Steinhoff, B. A.; Stahl, S. S. Org. Lett. 2002, 4, 4179.
    • (2002) Org. Lett. , vol.4 , pp. 4179
    • Steinhoff, B.A.1    Stahl, S.S.2
  • 25
    • 0242479002 scopus 로고    scopus 로고
    • note
    • 2, 7, and NaOt-Am resulted in only free phosphine and a small residual peak that cannot be identified at 48 ppm: no phosphine oxide was present in either mixture. Thus, it is difficult to draw conclusions on the basis of these studies.
  • 32
    • 0037125518 scopus 로고    scopus 로고
    • Similar KIEs have been observed for β-hydride elimination from metal-alkyl and metal-alkoxide complexes: (a) Mueller, J. A.; Jensen, D. R.; Sigman, M. S. J. Am. Chem. Soc. 2002. 124, 8202.
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 8202
    • Mueller, J.A.1    Jensen, D.R.2    Sigman, M.S.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.