A general synthesis of azetidines by copper-catalysed photoinduced anti-Baldwin radical cyclization of ynamides

A general anti-Baldwin radical 4-exo-dig cyclization from nitrogen-substituted alkynes is reported. Upon reaction with a heteroleptic copper complex in the presence of an amine and under visible light irradiation, a range of ynamides were shown to smoothly cyclize to the corresponding azetidines, us...

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Published in:Nature communications Vol. 13; no. 1; pp. 560 - 8
Main Authors: Jacob, Clément, Baguia, Hajar, Dubart, Amaury, Oger, Samuel, Thilmany, Pierre, Beaudelot, Jérôme, Deldaele, Christopher, Peruško, Stefano, Landrain, Yohann, Michelet, Bastien, Neale, Samuel, Romero, Eugénie, Moucheron, Cécile, Van Speybroeck, Veronique, Theunissen, Cédric, Evano, Gwilherm
Format: Journal Article
Language:English
Published: London Nature Publishing Group UK 28.01.2022
Nature Publishing Group
Nature Portfolio
Subjects:
119/118
639/638/403
639/638/403/933
639/638/77/890
Alkynes
Atmospheric chemistry
Catalysis
Chemical bonds
Chemical Sciences
Chemical synthesis
Construction
Coordination compounds
Copper
Copper compounds
Efficiency
Humanities and Social Sciences
Irradiation
Light irradiation
multidisciplinary
Natural products
Nitrogen
Photochemicals
Photoredox catalysis
Regioselectivity
Science
Science (multidisciplinary)
ISSN:2041-1723, 2041-1723
Online Access:Get full text
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Summary:A general anti-Baldwin radical 4-exo-dig cyclization from nitrogen-substituted alkynes is reported. Upon reaction with a heteroleptic copper complex in the presence of an amine and under visible light irradiation, a range of ynamides were shown to smoothly cyclize to the corresponding azetidines, useful building blocks in natural product synthesis and medicinal chemistry, with full control of the regioselectivity of the cyclization resulting from a unique and underrated radical 4-exo-dig pathway. The construction of four-membered rings via a 4-exo-dig cyclization was originally theorized to be unfavourable and only recently shown in sparse examples. Here the authors present a photochemical, radical 4-exo-dig cyclization of ynamides to form azetidines, promoted by copper photoredox catalysis.
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ISSN:2041-1723
2041-1723
DOI:10.1038/s41467-022-28098-x