Visible light triggered photo-decomposition of vinyl azides to (E)-stilbene derivatives via 1,2-acyl migration

An efficient photocatalyst-free visible light assisted synthetic route to various (E)-stilbene derivatives was developed. The reaction proceeds through a denitrogenative photo-decomposition of vinyl azides into 2H-azirines followed by neighboring amino group assisted ring opening, 1,2-acyl migration...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2019-06, Vol.17 (24), p.5971-5981
Main Authors: Borra, Satheesh, Borkotoky, Lodsna, Newar, Uma Devi, Kalwar, Anshu, Das, Babulal, Maurya, Ram Awatar
Format: Article
Language:English
Subjects:
Crystallography
Decomposition
Decomposition reactions
Derivatives
Migration
NMR
Nuclear magnetic resonance
Photocatalysts
Photochemical reactions
Photochemicals
Ring opening
Single crystals
Stilbene
trans-Stilbene
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Summary:An efficient photocatalyst-free visible light assisted synthetic route to various (E)-stilbene derivatives was developed. The reaction proceeds through a denitrogenative photo-decomposition of vinyl azides into 2H-azirines followed by neighboring amino group assisted ring opening, 1,2-acyl migration and enolization. The photochemical reaction offers light harvesting without any photocatalyst to access a wide variety of substituted (E)-stilbenes in moderate to high yields.
ISSN:1477-0520
1477-0539
DOI:10.1039/c9ob01035a