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Title: Reduction of Carbonyl Groups by Uranium(III) and Formation of a Stable Amide Radical Anion

Abstract

Abstract Methyl benzoate, N , N ‐dimethylbenzamide, and benzophenone were reduced by U III [N(SiMe 3 ) 2 ] 3 resulting in uranium(IV) products. Reduction of benzophenone lead to U IV [OC ⋅ Ph 2 )][N(SiMe 3 ) 2 ] 3 , ( 1.1 ) which forms the dinuclear complex, [N(SiMe 3 ) 2 ] 3 U IV (OCPhPh‐CPh 2 O)U IV [N(SiMe 3 ) 2 ] 3 ( 1.2 ), through coupling of the ketyl radical species upon crystallization. Reaction of N , N ‐dimethylbenzamide with U III [N(SiMe 3 ) 2 ] 3 resulted in U IV [OC ⋅ (Ph)(NMe 2 )][N(SiMe 3 ) 2 ] 3 ( 2 ), a uranium(IV) compound and the first example of a charge‐separated amide radical. In the case of methyl benzoate, the reduction resulted in U IV (OMe)[N(SiMe 3 ) 2 ] 3 ( 3 ) and benzaldehyde as the reduced organic fragment. Compound 2 showed the ability to act as a uranium(III) synthon in its reactivity with trimethylsilyl azide, a reaction that yielded U V (=NSiMe 3 )[N(SiMe 3 ) 2 ] 3 . Additionally, 2 was reduced with potassium graphite resulting in [U(μ‐O)[O=C(NMe 2 )(Ph)][N(SiMe 3 ) 2 ]more » 2 ] 2 ( 4 ), a dinuclear uranium compound bridged by oxo ligands. Reduction of 2 in the presence of 15‐crown‐5 afforded isolation of the mono‐oxo compound, [(15‐crown‐5) 2 K][UO[N(SiMe 3 ) 2 ] 3 ] ( 5 ). The results expand the reduction capabilities of U III complexes and demonstrate a strategy for isolating novel metal‐stabilized radicals.« less

Authors:
 [1]; ORCiD logo [1];  [2];  [1];  [1]; ORCiD logo [1]
+ Show Author Affiliations
  1. Univ. of Pennsylvania, Philadelphia, PA (United States)
  2. Univ. of Pennsylvania, Philadelphia, PA (United States); Children's Hospital of Philadelphia, PA (United States)
Publication Date:
Research Org.:
Energy Frontier Research Centers (EFRC) (United States). Center for Actinide Science & Technology (CAST)
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES)
OSTI Identifier:
1470214
Alternate Identifier(s):
OSTI ID: 1412572
Grant/Contract Number:  
SC0016568
Resource Type:
Accepted Manuscript
Journal Name:
Chemistry - A European Journal
Additional Journal Information:
Journal Volume: 24; Journal Issue: 4; Journal ID: ISSN 0947-6539
Publisher:
ChemPubSoc Europe
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; EPR spectroscopy; radicals; reactive intermediates; redox chemistry; uranium

Citation Formats

Mullane, Kimberly C., Cheisson, Thibault, Nakamaru-Ogiso, Eiko, Manor, Brian C., Carroll, Patrick J., and Schelter, Eric J. Reduction of Carbonyl Groups by Uranium(III) and Formation of a Stable Amide Radical Anion. United States: N. p., 2017. Web. doi:10.1002/chem.201703396.
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Mullane, Kimberly C., Cheisson, Thibault, Nakamaru-Ogiso, Eiko, Manor, Brian C., Carroll, Patrick J., & Schelter, Eric J. Reduction of Carbonyl Groups by Uranium(III) and Formation of a Stable Amide Radical Anion. United States. https://doi.org/10.1002/chem.201703396
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Mullane, Kimberly C., Cheisson, Thibault, Nakamaru-Ogiso, Eiko, Manor, Brian C., Carroll, Patrick J., and Schelter, Eric J. Tue . "Reduction of Carbonyl Groups by Uranium(III) and Formation of a Stable Amide Radical Anion". United States. https://doi.org/10.1002/chem.201703396. https://www.osti.gov/servlets/purl/1470214.
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@article{osti_1470214,
title = {Reduction of Carbonyl Groups by Uranium(III) and Formation of a Stable Amide Radical Anion},
author = {Mullane, Kimberly C. and Cheisson, Thibault and Nakamaru-Ogiso, Eiko and Manor, Brian C. and Carroll, Patrick J. and Schelter, Eric J.},
abstractNote = {Abstract Methyl benzoate, N , N ‐dimethylbenzamide, and benzophenone were reduced by U III [N(SiMe 3 ) 2 ] 3 resulting in uranium(IV) products. Reduction of benzophenone lead to U IV [OC ⋅ Ph 2 )][N(SiMe 3 ) 2 ] 3 , ( 1.1 ) which forms the dinuclear complex, [N(SiMe 3 ) 2 ] 3 U IV (OCPhPh‐CPh 2 O)U IV [N(SiMe 3 ) 2 ] 3 ( 1.2 ), through coupling of the ketyl radical species upon crystallization. Reaction of N , N ‐dimethylbenzamide with U III [N(SiMe 3 ) 2 ] 3 resulted in U IV [OC ⋅ (Ph)(NMe 2 )][N(SiMe 3 ) 2 ] 3 ( 2 ), a uranium(IV) compound and the first example of a charge‐separated amide radical. In the case of methyl benzoate, the reduction resulted in U IV (OMe)[N(SiMe 3 ) 2 ] 3 ( 3 ) and benzaldehyde as the reduced organic fragment. Compound 2 showed the ability to act as a uranium(III) synthon in its reactivity with trimethylsilyl azide, a reaction that yielded U V (=NSiMe 3 )[N(SiMe 3 ) 2 ] 3 . Additionally, 2 was reduced with potassium graphite resulting in [U(μ‐O)[O=C(NMe 2 )(Ph)][N(SiMe 3 ) 2 ] 2 ] 2 ( 4 ), a dinuclear uranium compound bridged by oxo ligands. Reduction of 2 in the presence of 15‐crown‐5 afforded isolation of the mono‐oxo compound, [(15‐crown‐5) 2 K][UO[N(SiMe 3 ) 2 ] 3 ] ( 5 ). The results expand the reduction capabilities of U III complexes and demonstrate a strategy for isolating novel metal‐stabilized radicals.},
doi = {10.1002/chem.201703396},
journal = {Chemistry - A European Journal},
number = 4,
volume = 24,
place = {United States},
year = {Tue Sep 05 00:00:00 EDT 2017},
month = {Tue Sep 05 00:00:00 EDT 2017}
}
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    • DOI: 10.1039/d0sc01349h

    Ultrafast Amidation of Esters using Lithium Amides under Aerobic Ambient Temperature Conditions in Sustainable Solvents
    text, January 2020

    • Fairley, Michael; Bole, Leonie Julia; Mulks, Florian Felix
    • The Royal Society of Chemistry
    • DOI: 10.48350/155335
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