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As a part of extensive work on homolytic aromatic substitution (HAS), Minisci has reported the oxidative coupling of alkylamides with N -heteroarenes such as pyridine in the use of a peroxy oxidant including t -BuOO t -Bu, but the scope of arenes is limited to pyridine derivatives, which as protonated forms accept addition of nucleophilic acylaminomethyl radical intermediates.;, For a review on HAS:; Heterocycles 1989, 28, 489-519 For an iron-catalyzed reaction:; J. Chem. Soc., Chem. Commun. 1983, 916-917
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As a part of extensive work on homolytic aromatic substitution (HAS), Minisci has reported the oxidative coupling of alkylamides with N -heteroarenes such as pyridine in the use of a peroxy oxidant including t -BuOO t -Bu, but the scope of arenes is limited to pyridine derivatives, which as protonated forms accept addition of nucleophilic acylaminomethyl radical intermediates. Arnone, A.; Cecere, M.; Galli, R.; Minisci, F.; Perchinunno, M.; Porta, O.; Gardini, G. Gazz. Chim. Ital. 1973, 103, 13-29 For a review on HAS: Minisci, F.; Vismara, E.; Fontana, F. Heterocycles 1989, 28, 489-519 For an iron-catalyzed reaction: Citterio, A.; Gentile, A.; Minisci, F.; Serravalle, M.; Ventura, S. J. Chem. Soc., Chem. Commun. 1983, 916-917
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9744257740
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Fogg and dos Santos call this, in their review, "auto-tandem catalysis" with the definition "processes of this type involve two or more mechanistically distinct catalyses promoted by a single catalyst precursor: both cycles occur spontaneously by cooperative interaction of the various species (catalyst, substrate, additional reagents if required) present at the outset of reaction.", For other recent reviews on tandem catalysis, see:; Chem. Rev. 2005, 105, 1001-1020
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Fogg and dos Santos call this, in their review, "auto-tandem catalysis" with the definition "processes of this type involve two or more mechanistically distinct catalyses promoted by a single catalyst precursor: both cycles occur spontaneously by cooperative interaction of the various species (catalyst, substrate, additional reagents if required) present at the outset of reaction." Fogg, D. E.; dos Santos, E. N. Coord. Chem. Rev. 2004, 248, 2365-2379 For other recent reviews on tandem catalysis, see: Wasilke, J.-C.; Obrey, S. J.; Baker, R. T.; Bazan, G. C. Chem. Rev. 2005, 105, 1001-1020
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78650857653
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The reaction of 3m with 2a in the presence of HCl (1 mol %) under the same conditions (40 °C, 2 h, DCE) gave 4am in 2% yield (5% conv).
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The reaction of 3m with 2a in the presence of HCl (1 mol %) under the same conditions (40 °C, 2 h, DCE) gave 4am in 2% yield (5% conv).
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37
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78650877062
-
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2-catalyzed coupling of 1d with 3n, which is less nucleophilic than 3m, scored a lower yield (46%) under the same conditions as entry 6 of Table 3.
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2-catalyzed coupling of 1d with 3n, which is less nucleophilic than 3m, scored a lower yield (46%) under the same conditions as entry 6 of Table 3.
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