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Volumn 26, Issue 15, 2007, Pages 3746-3754

Synthesis and characterization of palladium(II) πr-allyl complexes with chiral phosphinocarbene ligands. Kinetics and mechanism of allylic amination

Author keywords

[No Author keywords available]

Indexed keywords

AMINATION; CHIRALITY; ENANTIOSELECTIVITY; LIGANDS; REACTION KINETICS; SYNTHESIS (CHEMICAL);

EID: 34547476609     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om0702126     Document Type: Article
Times cited : (60)

References (84)
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    • (a) Togni, A., Hayashi, T., Eds. Ferrocenes; VCH: Weinheim, 1995.
    • (1995) Ferrocenes
  • 53
    • 34547451625 scopus 로고    scopus 로고
    • A similar spectrum was recently observed for a Cu complex with the parent tridentate PCP ligands and explained with a relatively weak Cu, P bond, leading to a dynamic behavior Gishig, S, Togni, A. Organometallics 2005, 24, 203
    • A similar spectrum was recently observed for a Cu complex with the parent tridentate PCP ligands and explained with a relatively weak Cu - P bond, leading to a dynamic behavior (Gishig, S.; Togni, A. Organometallics 2005, 24, 203).
  • 58
    • 34547414951 scopus 로고    scopus 로고
    • Douthwhite et al. supposed the existence of these species as intermediates in the reaction of allylic alkylation using iminocarbene ligands see ref 7a
    • Douthwhite et al. supposed the existence of these species as intermediates in the reaction of allylic alkylation using iminocarbene ligands (see ref 7a).
  • 59
    • 34547431036 scopus 로고    scopus 로고
    • Ph.D. Thesis no. 12167, ETH Zurich
    • Burckhart, U, Ph.D. Thesis no. 12167, ETH Zurich, 1997.
    • (1997)
    • Burckhart, U.1
  • 60
    • 34547423294 scopus 로고    scopus 로고
    • This signal is visible only for the major exo isomer
    • This signal is visible only for the major exo isomer.
  • 63
    • 0003417469 scopus 로고
    • Trost, B. M, Fleming, I, Semmelbach, M. F, Eds, Pergamon: Oxford, U.K
    • (b) Godleski, S. A. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Semmelbach, M. F., Eds.; Pergamon: Oxford, U.K., 1991.
    • (1991) Comprehensive Organic Synthesis
    • Godleski, S.A.1
  • 70
    • 33845379753 scopus 로고
    • 2046. For a general treatment of the Curtin-Hammett principle, see
    • (b) Mackenzie, P. B.; Whelan, J.; Bosnich, P. J. J. Am. Chem. Soc. 1985, 107, 2046. For a general treatment of the Curtin-Hammett principle, see:
    • (1985) J. Am. Chem. Soc , vol.107
    • Mackenzie, P.B.1    Whelan, J.2    Bosnich, P.J.3
  • 72
    • 34547469466 scopus 로고    scopus 로고
    • At 25°C the pKa values for piperidine and benzylamine are 11.12 and 9.34, respectively Albert, A, Serjeant, E. P. In The Determination of Ionization Constant; Chapman and Hall: London, 1984; p 151
    • a values for piperidine and benzylamine are 11.12 and 9.34, respectively (Albert, A.; Serjeant, E. P. In The Determination of Ionization Constant; Chapman and Hall: London, 1984; p 151.
  • 76
    • 34547461671 scopus 로고    scopus 로고
    • For example [Pd-(η3-allyl)(NHR2) 2, are pratically inert toward nucleophilic attack see ref 30a
    • + are pratically inert toward nucleophilic attack (see ref 30a).
  • 80
    • 34547470475 scopus 로고    scopus 로고
    • The unreacted 1,3-diphenylallylethyl carbonate was still racemic
    • The unreacted 1,3-diphenylallylethyl carbonate was still racemic.
  • 81
    • 34547403084 scopus 로고    scopus 로고
    • It seems improbable that the minor isomers may display such different rates for the nucleophilic attack to compensate for a possible preferential attack at one allylic terminus in the major isomer. Indeed, the case of a pyrazole-phosphine complex with an isomeric distribution very similar to 6f was reported, for which a preferential attack at the carbon trans to phosphorus led to high ee's see ref 11a
    • It seems improbable that the minor isomers may display such different rates for the nucleophilic attack to compensate for a possible preferential attack at one allylic terminus in the major isomer. Indeed, the case of a pyrazole-phosphine complex with an isomeric distribution very similar to 6f was reported, for which a preferential attack at the carbon trans to phosphorus led to high ee's (see ref 11a).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.