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Volumn 49, Issue 17, 2010, Pages 3045-3048

Tunable bromomagnesium thiolate tishchenko reaction catalysts: Intermolecular aldehyde-trifluoromethylketone coupling

Author keywords

Disproportionation; Grignard reagents; Homogeneous catalysis; Synthetic methods; Tishchenko reaction

Indexed keywords

BIOCHEMICAL PROCESS; COUPLING REACTION; DISPROPORTIONATIONS; GRIGNARD REAGENT; HOMOGENEOUS CATALYSIS; REACTION MECHANISM; SYNTHETIC METHODS; THIOLATES; TRIFLUOROMETHYLKETONE;

EID: 77951190429     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.200907167     Document Type: Article
Times cited : (54)

References (48)
  • 14
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    • A number of heterogeneous catalysts for the Tishchenko reaction, have also been, disclosed, for details see ref. [3a]
    • A number of heterogeneous catalysts for the Tishchenko reaction, have also been, disclosed, for details see ref. [3a].
  • 22
    • 34547177285 scopus 로고    scopus 로고
    • Two other recent strategies involving group I metal salts as catalysts are noteworthy: Abaee et al. demonstrated that LiBr could act as an. effective Tishchenko catalyst for the dimerization of aromatic aldehydes if used at 50 mol% levels under solvent free conditions (liquid substrates essential), while Mack and Waddell found that NaH catalyzed the same reaction class at 10 mol % loading if used in the absence of solvent in a ball mill, see : a) M. M. Mojtahedi, E. Akbarzadeh, R. Sharifi, M. S. Abaee, Org. Lett. 2007, 9, 2791;
    • (2007) Org. Lett. , vol.9 , pp. 2791
    • Mojtahedi, M.M.1    Akbarzadeh, E.2    Sharifi, R.3    Abaee, M.S.4
  • 31
    • 77951161765 scopus 로고    scopus 로고
    • Several variants of this general mechanism have been proposed, for a discussion see Ref. [3]
    • Several variants of this general mechanism have been proposed, for a discussion see Ref. [3].
  • 32
    • 0035861769 scopus 로고    scopus 로고
    • Intramolecular cross-coupling is known: Fang et al. demonstrated that six-membered lactones can be synthesized by intramolecular Tishchenko coupling of an aldehyde and a ketone, however no examples of a corresponding intermolecular process were reported, see: a) J. L. Hsu, J. M. Fang, J. Org. Chem. 2001, 66, 8573;
    • (2001) J. Org. Chem. , vol.66 , pp. 8573
    • Hsu, J.L.1    Fang, J.M.2
  • 34
    • 33750880138 scopus 로고    scopus 로고
    • It should be noted that the term "cross-coupling" is used in a Tishchenko reaction context and does not refer to Tishchenko variants such as the Tishchenko-aldol (for a review see Ref. [14a]) or Tishchenko-Michael (for an example see Ref. [14b]) reactions: a) J. Mlynarski, Eur. J. Org. Chem. 2006, 4779;
    • (2006) Eur. J. Org. Chem. , pp. 4779
    • Mlynarski, J.1
  • 39
    • 77951158239 scopus 로고    scopus 로고
    • For representative examples of thiolate catalysis of Michael addition reactions see: a) J. K. Ergtlden, H. W. Moore, Org. Lett. 1.999, 7, 375;
    • (1999) Org. Lett. , vol.7 , pp. 375
    • Ergtlden, J.K.1    Moore, H.W.2
  • 41
    • 84943509126 scopus 로고
    • A related intramolecular version of this process had been suggested to explain thiol catalysis of apparent transfer of hydride in glyoxal derivarives; however, this was later shown to occur through a proton-transfer mechanism, see: a) V. Franzen, Chem. Ber. 1955, 88, 1361;
    • (1955) Chem. Ber. , vol.88 , pp. 1361
    • Franzen, V.1
  • 45
    • 0035861769 scopus 로고    scopus 로고
    • 2 (40-50 mol%) were generally required for efficient cyclization and no intermolecular variants were reported, see : J. L. Hsu, J. M. Fang, J. Org. Chem. 2001, 66, 8573.
    • (2001) J. Org. Chem. , vol.66 , pp. 8573
    • Hsu, J.L.1    Fang, J.M.2
  • 46
    • 77951153318 scopus 로고    scopus 로고
    • 2, MeCN, PhMe, or EtOAc
    • 2, MeCN, PhMe, or EtOAc.
  • 47
    • 77951175866 scopus 로고    scopus 로고
    • 1H NMR spectroscopy, and their catalytic competency was confirmed by crossover experiments. See the Supporting Information for details
    • 1H NMR spectroscopy, and their catalytic competency was confirmed by crossover experiments. See the Supporting Information for details.
  • 48
    • 77951174075 scopus 로고    scopus 로고
    • We found that the reaction did not proceed with less electrophilic ketones such as acetophenone under any condition, set evaluated
    • We found that the reaction did not proceed with less electrophilic ketones such as acetophenone under any condition, set evaluated.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.