Heterogeneous Catalytic Oxidation of Amides to Imides by Manganese Oxides
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.
- Authors:
-
- Univ. of Connecticut, Storrs, CT (United States). Dept. of Chemistry
- Univ. of Connecticut, Storrs, CT (United States). Inst. of Materials Science
- ExxonMobil Research and Engineering Company, Annandale, NJ (United States). Corporate Strategic Research
- Univ. of Connecticut, Storrs, CT (United States). Dept. of Chemistry. Inst. of Materials Science
- Publication Date:
- Research Org.:
- Univ. of Connecticut, Storrs, CT (United States); ExxonMobil Research and Engineering Company, Annandale, NJ (United States)
- Sponsoring Org.:
- USDOE Office of Science (SC), Basic Energy Sciences (BES). Chemical Sciences, Geosciences, and Biosciences Division; ExxonMobil Research and Engineering Company
- OSTI Identifier:
- 1500003
- Grant/Contract Number:
- FG02-86ER13622
- Resource Type:
- Accepted Manuscript
- Journal Name:
- Scientific Reports
- Additional Journal Information:
- Journal Volume: 8; Journal ID: ISSN 2045-2322
- Publisher:
- Nature Publishing Group
- Country of Publication:
- United States
- Language:
- English
- Subject:
- 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; heterogeneous catalysis; porous materials
Citation Formats
Biswas, Sourav, Khanna, Harshul S., Nizami, Quddus A., Caldwell, Donald R., Cavanaugh, Katherine T., Howell, Amy R., Raman, Sumathy, Suib, Steven L., and Nandi, Partha. Heterogeneous Catalytic Oxidation of Amides to Imides by Manganese Oxides. United States: N. p., 2018.
Web. doi:10.1038/s41598-018-31729-3.
Biswas, Sourav, Khanna, Harshul S., Nizami, Quddus A., Caldwell, Donald R., Cavanaugh, Katherine T., Howell, Amy R., Raman, Sumathy, Suib, Steven L., & Nandi, Partha. Heterogeneous Catalytic Oxidation of Amides to Imides by Manganese Oxides. United States. https://doi.org/10.1038/s41598-018-31729-3
Biswas, Sourav, Khanna, Harshul S., Nizami, Quddus A., Caldwell, Donald R., Cavanaugh, Katherine T., Howell, Amy R., Raman, Sumathy, Suib, Steven L., and Nandi, Partha. Tue .
"Heterogeneous Catalytic Oxidation of Amides to Imides by Manganese Oxides". United States. https://doi.org/10.1038/s41598-018-31729-3. https://www.osti.gov/servlets/purl/1500003.
@article{osti_1500003,
title = {Heterogeneous Catalytic Oxidation of Amides to Imides by Manganese Oxides},
author = {Biswas, Sourav and Khanna, Harshul S. and Nizami, Quddus A. and Caldwell, Donald R. and Cavanaugh, Katherine T. and Howell, Amy R. and Raman, Sumathy and Suib, Steven L. and Nandi, Partha},
abstractNote = {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.},
doi = {10.1038/s41598-018-31729-3},
journal = {Scientific Reports},
number = ,
volume = 8,
place = {United States},
year = {Tue Sep 11 00:00:00 EDT 2018},
month = {Tue Sep 11 00:00:00 EDT 2018}
}
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Figures / Tables:
Table 1: Optimization of oxidation of N-benzylbenzamide. aReaction conditions: N-benzyl benzamide (100 mg, 0.5 mmol, 1.0 equiv), meso Cs/Mn2O3 (50 mg), acetonitrile (5 mL, 95 mmol, 190 equiv), 80 °C, TBHP (5 mmol, 0.45 g, 10 equiv), 22 h. bConversions and selectivities were determined by GC-MS based on concentration ofmore »
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