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Volumn 12, Issue 3, 2006, Pages 949-955

Novel anti-Markovnikov regioselectivity in the Wacker reaction of styrenes

Author keywords

Homogeneous catalysis; Palladium; Reaction mechanisms; Styrenes; Wacker reaction

Indexed keywords

ALDEHYDES; CATALYSTS; CHEMICAL REACTIONS; OXIDATION; PALLADIUM; REACTION KINETICS; STEREOCHEMISTRY;

EID: 30744475459     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200400644     Document Type: Article
Times cited : (82)

References (63)
  • 6
    • 0003690482 scopus 로고
    • D. Riedel Pub. Co., Dordrecht (Netherlands)
    • For an overview of the lead mechanistic studies on the Wacker reaction to 1980, see: P. M. Henry, Palladium Catalyzed Oxidation of Hydrocarbons, D. Riedel Pub. Co., Dordrecht (Netherlands), 1980.
    • (1980) Palladium Catalyzed Oxidation of Hydrocarbons
    • Henry, P.M.1
  • 8
    • 85083243520 scopus 로고
    • For reviews see: a) J. Tsuji. Synthesis 1984, 369-384;
    • (1984) Synthesis , pp. 369-384
    • Tsuji, J.1
  • 21
    • 33845375365 scopus 로고
    • Keinan has reported anti-Markovnikov regioselectivity in the Wacker oxidation of β-methylstyrenes, in this case due to the influence of heteroatoms: E. Keinan, K. K. Seth, R. Lamed, J. Am. Chem. Soc. 1986, 108, 3474-3480.
    • (1986) J. Am. Chem. Soc. , vol.108 , pp. 3474-3480
    • Keinan, E.1    Seth, K.K.2    Lamed, R.3
  • 22
    • 79957618467 scopus 로고
    • The mechanism of the Wacker reaction has been investigated mainly with ethene and higher homologues. There have been a small number of studies of the mechanism of the Wacker reaction of styrenes. These have been mainly carried out in largely aqueous media, see: a) L. M. Zakharova, M. N. Vargaftik, I. I. Moiseev, L. A. Katsman, Izv. Akad. Nauk SSSR Ser. Khim. 1970, 700-702:
    • (1970) Izv. Akad. Nauk SSSR Ser. Khim. , pp. 700-702
    • Zakharova, L.M.1    Vargaftik, M.N.2    Moiseev, I.I.3    Katsman, L.A.4
  • 25
    • 30744455389 scopus 로고
    • Kinet. Catal. 1969, 10, 736-744;
    • (1969) Kinet. Catal. , vol.10 , pp. 736-744
  • 27
    • 30744444846 scopus 로고
    • Kinet. Catal. 1989, 30, 1298-1299;
    • (1989) Kinet. Catal. , vol.30 , pp. 1298-1299
  • 35
    • 0000295212 scopus 로고
    • Unless otherwise started, product ratios were determined by gas chromatography (sec Experimental Section). Authentic samples of products 3a and 3b, necessary for calibration of the gas chromatography system, were produced by IBX oxidation of the corresponding commercial alcohols. See: a) M. Frigerio, M. Santagostino, S. Sputore, G. Palmisano, J. Org. Chem. 1995, 60, 7272-7727;
    • (1995) J. Org. Chem. , vol.60 , pp. 7272-7727
    • Frigerio, M.1    Santagostino, M.2    Sputore, S.3    Palmisano, G.4
  • 38
    • 30744463821 scopus 로고    scopus 로고
    • note
    • 2). Conversion of the starting material was obviously lowered.
  • 39
    • 30744436737 scopus 로고    scopus 로고
    • note
    • The reactions were carried out under a nitrogen atmosphere, in freeze-pump degassed solvents. In the presence of oxygen, the aldehyde products were found to be rapidly degraded to the analogous benzaldehydes. This reaction occurred even in the absence of palladium(II). but was markedly accelerated by the presence of the metal salt.
  • 40
    • 30744452150 scopus 로고    scopus 로고
    • note
    • 2). The addition of external ligand sources, such as LiCl, also led to preferential formation of ketones.
  • 50
    • 30744478138 scopus 로고    scopus 로고
    • note
    • The unknown quantity of water in the HPA makes exact stoichiometry difficult to assess.
  • 61
    • 30744465243 scopus 로고    scopus 로고
    • note
    • Cooling the neat alcohol in ice led to the liquid freezing.
  • 62
    • 30744437833 scopus 로고    scopus 로고
    • note
    • THF was used as the substrate was insoluble in neat DMF.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.