Organic Letters, volume 24, issue 49, pages 8942-8947
Decatungstate-Catalyzed Photochemical Synthesis of Enaminones from Vinyl Azides and Aldehydes
Publication type: Journal Article
Publication date: 2022-11-18
Journal:
Organic Letters
scimago Q1
wos Q1
SJR: 1.245
CiteScore: 9.3
Impact factor: 4.9
ISSN: 15237060, 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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