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  An Adaptive Rhodium Catalyst to Control the Hydrogenation Network of Nitroarenes

Chugh, V., Chatterjee, B., Chang, W.-C., Cramer, H. H., Hindemith, C., Randel, H., et al. (2022). An Adaptive Rhodium Catalyst to Control the Hydrogenation Network of Nitroarenes. Angewandte Chemie International Edition, 61(36): e202205515. doi:10.1002/anie.202205515.

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 Creators:
Chugh, Vishal1, 2, Author
Chatterjee, Basujit1, 2, Author
Chang, Wei-Chieh1, 2, Author
Cramer, Hanna H.1, Author
Hindemith, Carsten1, 2, Author
Randel, Helena1, 2, Author
Weyhermüller, Thomas1, Author
Farès, Christophe3, Author           
Werlé, Christophe1, 2, Author
Affiliations:
1Max Planck Institute for Chemical Energy Conversion, Stiftstr. 34–36, 45470 Mülheim an der Ruhr, Germany, ou_persistent22              
2Ruhr University Bochum, Universitätsstr. 150, 44801 Bochum, Germany, ou_persistent22              
3Service Department Farès (NMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445623              

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Free keywords: Adaptive Catalysis; Anilines; Hydrogenation; Hydroxylamines; Nitroarenes
 Abstract: An adaptive catalytic system that provides control over the nitroarene hydrogenation network to prepare a wide range of aniline and hydroxylamine derivatives is presented. This system takes advantage of a delicate interplay between a rhodium(III) center and a Lewis acidic borane introduced in the secondary coordination sphere of the metal. The high chemoselectivity of the catalyst in the presence of various potentially vulnerable functional groups and its readiness to be deployed at a preparative scale illustrate its practicality. Mechanistic studies and density functional theory (DFT) methods were used to shed light on the mode of functioning of the catalyst and elucidate the origin of adaptivity. The competition for interaction with boron between a solvent molecule and a substrate was found crucial for adaptivity. When operating in THF, the reduction network stops at the hydroxylamine platform, whereas the reaction can be directed to the aniline platform in toluene.

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Language(s): eng - English
 Dates: 2022-04-142022-06-272022-09-05
 Publication Status: Published in print
 Pages: 10
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1002/anie.202205515
 Degree: -

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Title: Angewandte Chemie International Edition
  Abbreviation : Angew. Chem., Int. Ed.
Source Genre: Journal
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Publ. Info: Weinheim : Wiley-VCH
Pages: - Volume / Issue: 61 (36) Sequence Number: e202205515 Start / End Page: - Identifier: ISSN: 1433-7851
CoNE: https://pure.mpg.de/cone/journals/resource/1433-7851