Halogenating Reagent‐Triggered Annulation of Propargylic Amides With Carbon Dioxide Leading to 5‐(Halomethylene)Oxazolidine‐2,4‐diones

ABSTRACT The conversion of CO 2 into value‐added chemicals represents a promising strategy for sustainable synthesis. Herein, we report a natural light‐promoted cyclization of propargylic amides with CO 2 using commonly used halogenating reagents as both the reaction promoter and halogen source to access 5‐(halomethylene)oxazolidine‐2,4‐diones, which enables the one‐pot construction of C─O, C─N, and C─X bonds. The protocol accommodates a broad range of substrates, and a variety of functional groups are well‐tolerated under mild reaction conditions, providing access to functionalized oxazolidine‐2,4‐diones up to 92% yield as single E isomers. The mechanistic experiments reveal that the reaction may proceed along two pathways, which are the radical pathway ( Path A ) and the halonium pathway ( Path B ). The resulting 5‐(halomethylene)oxazolidine‐2,4‐diones could be further transformed to complex molecules, highlighting the versatility.

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Publication Details

Journal
Chemistry - A European Journal
Published
2026-08-18
DOI
https://doi.org/10.1002/chem.71594
Primary Topic
Carbon dioxide utilization in catalysis
Type
article
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article

Halogenating Reagent‐Triggered Annulation of Propargylic Amides With Carbon Dioxide Leading to 5‐(Halomethylene)Oxazolidine‐2,4‐diones

Boyu Shi, Chanjuan Xi, Wenchao Lu, Chao Chen
Chemistry - A European Journal
Carbon dioxide utilization in catalysis
article

Halogenating Reagent‐Triggered Annulation of Propargylic Amides With Carbon Dioxide Leading to 5‐(Halomethylene)Oxazolidine‐2,4‐diones

Boyu Shi, Chanjuan Xi, Wenchao Lu, Chao Chen
article en

Abstract

ABSTRACT The conversion of CO 2 into value‐added chemicals represents a promising strategy for sustainable synthesis. Herein, we report a natural light‐promoted cyclization of propargylic amides with CO 2 using commonly used halogenating reagents as both the reaction promoter and halogen source to access 5‐(halomethylene)oxazolidine‐2,4‐diones, which enables the one‐pot construction of C─O, C─N, and C─X bonds. The protocol accommodates a broad range of substrates, and a variety of functional groups are well‐tolerated under mild reaction conditions, providing access to functionalized oxazolidine‐2,4‐diones up to 92% yield as single E isomers. The mechanistic experiments reveal that the reaction may proceed along two pathways, which are the radical pathway ( Path A ) and the halonium pathway ( Path B ). The resulting 5‐(halomethylene)oxazolidine‐2,4‐diones could be further transformed to complex molecules, highlighting the versatility.

Chemistry - A European Journal
Tsinghua University (CN)
Responsible consumption and production
Openalex Percentile: Top 22%
Carbon dioxide utilization in catalysis
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