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77951160229
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A number of heterogeneous catalysts for the Tishchenko reaction, have also been, disclosed, for details see ref. [3a]
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A number of heterogeneous catalysts for the Tishchenko reaction, have also been, disclosed, for details see ref. [3a].
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15
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0001477819
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For examples see: a) T. Ito, H. Horino, Y. Koshiro, A. Yamamoto, Bull. Chem. Soc Jpn. 1982, 55, 504;
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34547177285
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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;
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77951161765
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Several variants of this general mechanism have been proposed, for a discussion see Ref. [3]
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Several variants of this general mechanism have been proposed, for a discussion see Ref. [3].
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32
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0035861769
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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;
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33750880138
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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;
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77951158239
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For representative examples of thiolate catalysis of Michael addition reactions see: a) J. K. Ergtlden, H. W. Moore, Org. Lett. 1.999, 7, 375;
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84943509126
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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;
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65549105179
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For a recent enantioselective variant of the chemistry described in Ref. [22], see: E. Schmitt, I. Schiffers, C. BoIm, Tetrahedron Lett. 2009, 50, 3185.
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0035861769
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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.
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77951153318
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2, MeCN, PhMe, or EtOAc
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2, MeCN, PhMe, or EtOAc.
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47
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77951175866
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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.
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48
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77951174075
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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.
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