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Volumn 8, Issue 24, 2006, Pages 5557-5560

Development of a general Pd(II)-catalyzed intermolecular hydroalkoxylation reaction of vinylphenols by using a sacrificial alcohol as the hydride source

Author keywords

[No Author keywords available]

Indexed keywords

4 VINYLPHENOL; 4-VINYLPHENOL; ACETOPHENONE DERIVATIVE; ALCOHOL DERIVATIVE; HYDROGEN; PALLADIUM; PHENOL DERIVATIVE; SOLVENT; UNCLASSIFIED DRUG;

EID: 33846032298     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol062222t     Document Type: Article
Times cited : (46)

References (32)
  • 1
    • 15044351895 scopus 로고    scopus 로고
    • For recent reviews, see: a
    • For recent reviews, see: (a) Hultzsch, K. C. Adv. Synth. Catal. 2005, 347, 367.
    • (2005) Adv. Synth. Catal , vol.347 , pp. 367
    • Hultzsch, K.C.1
  • 10
    • 11844288364 scopus 로고    scopus 로고
    • For intramolecular hydroalkoxylation reactions, see: a
    • For intramolecular hydroalkoxylation reactions, see: (a) Oe, Y.; Ohta, T.; Ito, Y. Synlett 2005, 179.
    • (2005) Synlett , pp. 179
    • Oe, Y.1    Ohta, T.2    Ito, Y.3
  • 15
    • 3543083464 scopus 로고    scopus 로고
    • For intermolecular hydroalkoxylation reactions, see: f
    • For intermolecular hydroalkoxylation reactions, see: (f) Qian, H.; Han, X.; Widenhoefer, R. A. J. Am. Chem. Soc. 2004, 126, 9536.
    • (2004) J. Am. Chem. Soc , vol.126 , pp. 9536
    • Qian, H.1    Han, X.2    Widenhoefer, R.A.3
  • 18
    • 33749000858 scopus 로고    scopus 로고
    • Hartwig and co-workers have recently reported that metal-triflate- catalyzed hydroalkoxylation reactions may proceed by simple Brønsted acid catalysis. See: Rosenfeld, D. C, Shekhar, S, Takemiya, A, Utsunomiya, M, Hartwig, J. F. Org. Lett. 2006, 8, 4179-4282
    • Hartwig and co-workers have recently reported that metal-triflate- catalyzed hydroalkoxylation reactions may proceed by simple Brønsted acid catalysis. See: Rosenfeld, D. C.; Shekhar, S.; Takemiya, A.; Utsunomiya, M.; Hartwig, J. F. Org. Lett. 2006, 8, 4179-4282.
  • 20
    • 33645532122 scopus 로고    scopus 로고
    • For reviews of Pd(II)-catalyzed aerobic alcohol oxidation, see: (a) Sigman, M. S.; Jensen, D. R. Acc. Chem. Res. 2006, 39, 221.
    • For reviews of Pd(II)-catalyzed aerobic alcohol oxidation, see: (a) Sigman, M. S.; Jensen, D. R. Acc. Chem. Res. 2006, 39, 221.
  • 24
    • 0001530609 scopus 로고    scopus 로고
    • For difficulties in the oxidation of methanol with Pd(II) catalysts, see: (e) Lloyd, W. G. J. Org. Chem. 1967, 32, 2816.
    • For difficulties in the oxidation of methanol with Pd(II) catalysts, see: (e) Lloyd, W. G. J. Org. Chem. 1967, 32, 2816.
  • 27
    • 33845999052 scopus 로고    scopus 로고
    • See Supporting Information for details
    • See Supporting Information for details.
  • 28
    • 33845967224 scopus 로고    scopus 로고
    • The use of Pd, -sparteine]Cl2 as the catalyst results in a simultaneous oxidative kinetic resolution of sec-phenethyl alcohol with k rel values ∼10. See ref 7 for details
    • rel values ∼10. See ref 7 for details.
  • 29
    • 33845972387 scopus 로고    scopus 로고
    • The mixture of isotopomers is proposed to result from reversible hydride insertion see ref 6, A total of 91% incorporation of a single deuterium atom is observed and consistent with reversible hydride insertion that does not include dissociation of the olefin
    • The mixture of isotopomers is proposed to result from reversible hydride insertion (see ref 6). A total of 91% incorporation of a single deuterium atom is observed and consistent with reversible hydride insertion that does not include dissociation of the olefin.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.