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. 2018 Sep 11;8(1):13649.
doi: 10.1038/s41598-018-31729-3.

Heterogeneous Catalytic Oxidation of Amides to Imides by Manganese Oxides

Sourav Biswas  1   2 , Harshul S Khanna  3 , Quddus A Nizami  4 , Donald R Caldwell  1 , Katherine T Cavanaugh  1 , Amy R Howell  1 , Sumathy Raman  4 , Steven L Suib  5   6 , Partha Nandi  7
Affiliations

Heterogeneous Catalytic Oxidation of Amides to Imides by Manganese Oxides

Sourav Biswas et al. Sci Rep. .

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.

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Conflict of interest statement

The authors declare no competing interests.

Figures

Figure 1
Figure 1
Hammett plot of competitive oxidation of para substituted N-benzylbenzamide. Reaction conditions are as described in Table 3 for 8 h. A linear relationship between ln(kx/kH) and Brown–Okamoto constant (σp+) for para substituted benzylamines with slope (ρ) of 0.355 was obtained, which indicates the formation of a negatively charged transition state.
Figure 2
Figure 2
The C-H abstractions vs N-H abstraction pathways.
See this image and copyright information in PMC

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