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Volumn 26, Issue 24, 2007, Pages 5840-5847

Pd(0)-catalyzed phosphorus-carbon bond formation. Mechanistic and synthetic studies on the role of the palladium sources and anionic additives

Author keywords

[No Author keywords available]

Indexed keywords

ADDITIVES; BOND STRENGTH (CHEMICAL); CATALYST ACTIVITY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PALLADIUM COMPOUNDS;

EID: 36749062348     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om700797k     Document Type: Article
Times cited : (89)

References (52)
  • 16
    • 36749100454 scopus 로고    scopus 로고
    • Recent advances in organometallic chemistry directed towards organic synthesis
    • Recent advances in organometallic chemistry directed towards organic synthesis. Pure Appl. Chem. 2004, 76, No 3, 453-695.
    • (2004) Pure Appl. Chem , vol.76 , Issue.3 , pp. 453-695
  • 35
    • 37049111808 scopus 로고    scopus 로고
    • Catalytic effect of halides in cross-coupling reactions was first reported by T. Jeffery (Jeffery, T. J. Chem. Soc., Chem. Commun. 1984, 1287-1288). See also ref 38 for the use of halides in other cross-couplings and Heck reactions.
    • Catalytic effect of halides in cross-coupling reactions was first reported by T. Jeffery (Jeffery, T. J. Chem. Soc., Chem. Commun. 1984, 1287-1288). See also ref 38 for the use of halides in other cross-couplings and Heck reactions.
  • 41
    • 36749102478 scopus 로고    scopus 로고
    • 3N in the presence of an aryl halide.
    • 3N in the presence of an aryl halide.
  • 42
    • 36749052768 scopus 로고    scopus 로고
    • 3 was observed.
    • 3 was observed.
  • 43
    • 36749097786 scopus 로고    scopus 로고
    • Structures for an intermediate resonating at δp, 95.5 shown in Scheme 3 and the related intermediates in Scheme 5 are only tentative. These, and other low ligated intermediates discussed in this paper are, most likely stabilized via coordination of solvent molecules (that are omitted from the structures) and may have geometries different from those shown in the schemes
    • Structures for an intermediate resonating at δp = 95.5 shown in Scheme 3 and the related intermediates in Scheme 5 are only tentative. These, and other low ligated intermediates discussed in this paper are, most likely stabilized via coordination of solvent molecules (that are omitted from the structures) and may have geometries different from those shown in the schemes.
  • 44
    • 36749096166 scopus 로고    scopus 로고
    • - species apparently cannot be formed during the reductive elimination step of the catalytic cycle; otherwise, the H-phosphonate present would intercept it and arrest the catalytic reaction.
    • - species apparently cannot be formed during the reductive elimination step of the catalytic cycle; otherwise, the H-phosphonate present would intercept it and arrest the catalytic reaction.
  • 48
    • 36749074366 scopus 로고    scopus 로고
    • To be specific, a complex formed first in the oxidative addition is assumed to be a trigonal bipyramid PhPdII(PPh3) 2G1X that, in the presence of a minute amount of free PPh3 (which is the case for Pd(PPh3)4 or Pd(OAc)2, 3PPh3, quickly collapses to trans-PhPdII(PPh3)2G2 with the expulsion of G1 or X. For details, see refs 24 (review, 40 (G1, OAc, and 41 G1, Cl
    • 1 = Cl).
  • 51
    • 36749083335 scopus 로고    scopus 로고
    • -, and large differences in equilibria constants enable a practically quantitative replacement of the anion lower in the row with the one which is higher. See also refs 24 and 40.
    • -, and large differences in equilibria constants enable a practically quantitative replacement of the anion lower in the row with the one which is higher. See also refs 24 and 40.
  • 52
    • 36749058837 scopus 로고    scopus 로고
    • 2I in the reaction with styrene (syn-insertion step of the Heck reaction). See also ref 41.
    • 2I in the reaction with styrene (syn-insertion step of the Heck reaction). See also ref 41.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.