Organic Letters, volume 24, issue 49, pages 8942-8947

Decatungstate-Catalyzed Photochemical Synthesis of Enaminones from Vinyl Azides and Aldehydes

Publication typeJournal Article
Publication date2022-11-18
Journal: Organic Letters
scimago Q1
wos Q1
SJR1.245
CiteScore9.3
Impact factor4.9
ISSN15237060, 15237052
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
Visible light-induced synthesis of enaminones from vinyl azides and aldehydes under decatungstate photocatalysis was developed. The reaction proceeds via acyl radical generation from aldehyde, followed by its addition to vinyl azide, nitrogen elimination, hydrogen atom abstraction by the intermediate iminyl radical, and tautomerization. Photochemical synthesis was efficiently conducted under both batch and flow conditions. The method can be applied to various vinyl azides and aldehydes and provides the desired products in 15-72% yields.
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