Issue 8, 2017

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

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

Supplementary files

Article information

Article type
Edge Article
Submitted
15 Mar 2017
Accepted
05 Jun 2017
First published
12 Jun 2017
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2017,8, 5536-5546

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, 8, 5536 DOI: 10.1039/C7SC01175J

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