N‐Heterocyclic Carbene Catalyzed Ester Synthesis from Organic Halides through Incorporation of Oxygen Atoms from Air

Oxygenation reactions with molecular oxygen (O2) as the oxygen source provides a green and straightforward strategy for the construction of O‐containing compounds. Demonstrated here is a novel N‐heterocyclic carbene (NHC) catalyzed oxidative transformation of simple and readily available organic hal...

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Veröffentlicht in:Angewandte Chemie International Edition 2021-01, Vol.60 (4), p.2140-2144
Hauptverfasser: Tan, Hui, Wang, Shen‐An, Yan, Zixi, Liu, Jianzhong, Wei, Jialiang, Song, Song, Jiao, Ning
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Sprache:eng
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Zusammenfassung:Oxygenation reactions with molecular oxygen (O2) as the oxygen source provides a green and straightforward strategy for the construction of O‐containing compounds. Demonstrated here is a novel N‐heterocyclic carbene (NHC) catalyzed oxidative transformation of simple and readily available organic halides into valuable esters through the incorporation of O‐atoms from O2. Mechanistic studies prove that the deoxy Breslow intermediate generated in situ is oxidized to a Breslow intermediate for further transformation by this oxidative protocol. This method broadens the field of NHC catalysis and promotes oxygenation reactions with O2. A novel N‐heterocyclic carbene (NHC) catalyzed oxidative transformation of simple and readily available organic halides into valuable esters through the incorporation of O‐atoms from O2 was developed. This chemistry provides an efficient aerobic oxidative protocol for the oxidation of a deoxy Breslow intermediate into a Breslow intermediate for further transformation.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.202011039