Tris(pentafluorophenyl)borane‐Catalyzed Oxygen Insertion Reaction of α‐Diazoesters (α‐Diazoamides) with Dimethyl Sulfoxide

Tris(pentafluorophenyl)borane‐Catalyzed Oxygen Insertion Reaction of α‐Diazoesters (α‐Diazoamides) with Dimethyl Sulfoxide

A tris(pentafluorophenyl)borane‐catalyzed oxidation reaction of α‐diazoesters (α‐diazo amides) with dimethyl sulfoxide has been developed. The reaction proceeds under metal free conditions to afford a series α‐ketoesters and α‐ketoamides. The synthetic utility of this protocol is demonstrated throug...

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Veröffentlicht in:Advanced synthesis & catalysis 2022-02, Vol.364 (4), p.750-754
Hauptverfasser: Wu, Xiao‐Yang, Gao, Wen‐Xia, Zhou, Yun‐Bing, Liu, Miao‐Chang, Wu, Hua‐Yue
Format: Artikel
Sprache:eng
Schlagworte:
Amides
B(C6F5)3-catalyzed
Boranes
Dimethyl sulfoxide
metal-free condition
Oxidation
simple operation
Sulfoxides
α-diazo compounds
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Zusammenfassung:A tris(pentafluorophenyl)borane‐catalyzed oxidation reaction of α‐diazoesters (α‐diazo amides) with dimethyl sulfoxide has been developed. The reaction proceeds under metal free conditions to afford a series α‐ketoesters and α‐ketoamides. The synthetic utility of this protocol is demonstrated through synthetic transformations and scaled‐up synthesis.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.202101336