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Unprecedented selective homogeneous cobalt-catalysed reductive alkoxylation of cyclic imides under mild conditions

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Abstract

The first general and efficient non-noble metal-catalysed reductive C2-alkoxylation of cyclic imides (phthalimides and succinimides) is presented. Crucial for the success is the use of [Co(BF4)2·6H2O/triphos (L1)] combination and no external additives are required. Using the optimal cobalt-system, the hydrogenation of the aromatic ring of the parent phthalimide is avoided and only one of the carbonyl groups is selectively functionalized. The resulting products, N- and aryl-ring substituted 3-alkoxy-2,3-dihydro-1H-isoindolin-1-one and N-substituted 3-alkoxy-pyrrolidin-2-one derivatives, are prepared under mild conditions in good to excellent isolated yields. Intramolecular reductive couplings can also be performed affording tricyclic compounds in a one-step process. The present protocol opens the way to the development of new base-metal processes for the straightforward synthesis of functionalized N-heterocyclic compounds of pharmaceutical and biological interest.

Graphical abstract: Unprecedented selective homogeneous cobalt-catalysed reductive alkoxylation of cyclic imides under mild conditions

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Publication details

The article was received on 15 Mar 2017, accepted on 05 Jun 2017 and first published on 12 Jun 2017


Article type: Edge Article
DOI: 10.1039/C7SC01175J
Citation: Chem. Sci., 2017, Advance Article
  • Open access: Creative Commons BY license
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    Unprecedented selective homogeneous cobalt-catalysed reductive alkoxylation of cyclic imides under mild conditions

    J. R. Cabrero-Antonino, R. Adam, V. Papa, M. Holsten, K. Junge and M. Beller, Chem. Sci., 2017, Advance Article , DOI: 10.1039/C7SC01175J

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