Issue 6, 2022

Chemo-selective control of Ritter-type reaction by coordinatively unsaturated inorganic salt hydrates

Abstract

The Ritter-type reaction, without relying on a pre-installed functional group, is a highly efficient tool for the construction of amides. However, the intrinsic chemo-selectivity that determines the generation of amides or byproducts limits the efficiency and yield of the reaction. From 68 different types of hydrates, we found that a coordinatively unsaturated inorganic salt hydrate, MgSO4·2H2O, controlled chemo-selectivity and eliminated the shortcomings of other synthesis approaches. To rationalize the differences in selectivity of inorganic salt hydrates, we analyzed their corresponding water content, alkalinity, anions, and cations. MgSO4·2H2O was used with diverse scaffolds and C–H oxygenations, which demonstrated its generality in synthetic utility. Because it is readily available and it significantly improves yield, we expect that MgSO4·2H2O will have broad application for Ritter-type reactions.

Graphical abstract: Chemo-selective control of Ritter-type reaction by coordinatively unsaturated inorganic salt hydrates

Supplementary files

Article information

Article type
Research Article
Submitted
09 Dec 2021
Accepted
20 Jan 2022
First published
25 Jan 2022

Org. Chem. Front., 2022,9, 1541-1549

Chemo-selective control of Ritter-type reaction by coordinatively unsaturated inorganic salt hydrates

H. Lai, J. Xu, J. Lin, B. Su and D. Zha, Org. Chem. Front., 2022, 9, 1541 DOI: 10.1039/D1QO01832A

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