Copper-catalyzed synthesis of primary amides through reductive N-O cleavage of dioxazolones

A new method for the synthesis of primary amides is developed, in which dioxazolones are treated with a copper catalyst under mild reaction conditions. A broad scope of dioxazolones is exhibited as well as dioxazolones containing biologically active structural motifs. These robust and mild reaction...

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Bibliographic Details
Published in:RSC advances 2024-03, Vol.14 (14), p.944-9444
Main Authors: Bae, Hyeonwoong, Park, Jinhwan, Yoon, Rahyun, Lee, Seunghoon, Son, Jongwoo
Format: Article
Language:English
Subjects:
Aldehydes
Amides
Chemical synthesis
Chemistry
Copper
Functional groups
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Summary:A new method for the synthesis of primary amides is developed, in which dioxazolones are treated with a copper catalyst under mild reaction conditions. A broad scope of dioxazolones is exhibited as well as dioxazolones containing biologically active structural motifs. These robust and mild reaction conditions allow the transformation of dioxazolones to primary amides, in which sensitive functional groups such as hydroxyl, aldehyde, trialkylsilyl, and unsaturated carbon units are tolerated with excellent chemoselectivity. Reaction of dioxazolones in the presence of a copper catalyst and a silane is represented. Mild reductive reaction conditions for the N-O bond cleavage and large-scale protocols are also highlighted with excellent tolerance in the presence of water.
ISSN:2046-2069
2046-2069
DOI:10.1039/d4ra00320a