Chemoselective Oxyfunctionalization of Functionalized Benzylic Compounds with a Manganese Catalyst

Zhou, Jimei, Jia, Minxian, Song, Menghui, Huang, Zhiliang, Steiner, Alexander ORCID: 0000-0002-4315-6123, An, Qidong, Ma, Jianwei, Guo, Zhiyin, Zhang, Qianqian, Sun, Huaming
et al (show 4 more authors) (2022) Chemoselective Oxyfunctionalization of Functionalized Benzylic Compounds with a Manganese Catalyst. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 61 (30). e202205983-.

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Whilst allowing for easy access to synthetically versatile motifs and for modification of bioactive molecules, the chemoselective benzylic oxidation reactions of functionalized alkyl arenes remain challenging. Reported in this study is a new non-heme Mn catalyst stabilized by a bipiperidine-based tetradentate ligand, which enables methylene oxidation of benzylic compounds by H<sub>2</sub> O<sub>2</sub> , showing high activity and excellent chemoselectivity under mild conditions. The protocol tolerates an unprecedentedly wide range of functional groups, including carboxylic acid and derivatives, ketone, cyano, azide, acetate, sulfonate, alkyne, amino acid, and amine units, thus providing a low-cost, more sustainable and robust pathway for the facile synthesis of ketones, increase of complexity of organic molecules, and late-stage modification of drugs.

Item Type: Article
Uncontrolled Keywords: Benzylic Oxidation, Cyclic Imines, Ketones, Manganese Catalysts, Selective Oxidation
Divisions: Faculty of Science and Engineering > School of Physical Sciences
Depositing User: Symplectic Admin
Date Deposited: 08 Jul 2022 13:58
Last Modified: 18 Jan 2023 20:56
DOI: 10.1002/anie.202205983
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