Chemo-selective control of Ritter-type reaction by coordinatively unsaturated inorganic salt hydrates. Issue 6 (27th January 2022)

• Record Type: Journal Article
• Authors: Lai, Huifang; Xu, Jiexin; Lin, Jin; Su, Biling; Zha, Daijun
• Is Part Of: Organic chemistry frontiers. Volume 9:Issue 6(2022)
• Page Start: 1541
• Page End: 1549
• Publication Date: 2022-01-27
• Subjects: Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1039/d1qo01832a
• Languages: English
• ISSNs: 2052-4110

Abstract

Abstract : We used a readily available water source, MgSO4 ·2H2 O, to realize the control of the chemo-selectivity of the Ritter-type reaction efficiently. 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 ·2H2 O, 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 ·2H2 O 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 ·2H2 O will have broad application for Ritter-type reactions.