Abstract
Herein, we report a one-step peroxide mediated heterogeneous catalytic oxidation of amides to imides utilizing a series of manganese oxides. Among them, Cs/Mn2O3 was found to be the most active catalyst for the selective partial oxidation of N-benzylbenzamide to diphenyl imide. We have been able to apply an optimized oxidation method to other aromatic substrates. The feasibility of using air as an oxidant, the heterogeneous nature, inexpensive catalytic materials, respectable turnover numbers, and chemoselectivity to imides make this methodology an attractive choice for functional group transformations of amides to imides.
Highlights
Imide functional groups have versatile applications in pharmaceutical, polymer, and natural product synthesis[1,2]
Manganese oxide based materials have been utilized in different types of catalytic oxidation reactions such as selective oxidation of alcohols to aldehydes[19], hydrocarbons to alcohols and ketones[20], styrenes to styrene oxides[21], alcohols to amides[22,23,24,25,26], and amines to imines[27,28,29]
amorphous manganese oxide (AMO) oxidized a diverse array of aromatic amide derivatives to produce imides with high conversions and selectivities (90–100%)
Summary
Imide functional groups have versatile applications in pharmaceutical, polymer, and natural product synthesis[1,2]. The diversity of synthetic methods allows preparation of different forms of manganese oxide of varying porosity and crystallinity such as octahedral molecular sieves (OMS), octahedral layer (OL), amorphous manganese oxide (AMO), birnessite, α-manganese oxide, and mesoporous manganese oxide[11]. These mixed valent, high surface area materials have excellent redox properties which lead to highly efficient manganese based oxidation catalysts. We report a heterogeneous catalytic oxidation of benzylic amides to imides by two different classes of manganese oxides
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