Carbon Monoxide and Alkoxycarbonyl Radical Enabled Migration Strategy for the Carbonylative Functionalization of Unactivated Alkenes

Herein we report a "carbonylative migration" strategy for the acylation-esterification type double functionalization of unactivated alkenes using alkyloxalkyl chlorides and CO as the reagents. The transformation is proceeded by the alkoxycarbonyl radical addition to unactivated alkenes, followed by the insertion of carbon monoxide to induce intramolecular migration of heteroaryl groups, which is different from the traditional reaction modes. The reaction conditions were mild and well tolerated with varieties of functional groups. A variety of 1,4-dicarbonyl compounds with different ester groups were produced easily which has high potential applications in biology, medicine, and other fields.

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Publication Details

Journal
Chemistry - A European Journal
Published
2024-12-04
DOI
https://doi.org/10.1002/chem.202404113
Citations
3
Primary Topic
Radical Photochemical Reactions
Type
article
Field-Weighted Citation Impact
0.75

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article

Carbon Monoxide and Alkoxycarbonyl Radical Enabled Migration Strategy for the Carbonylative Functionalization of Unactivated Alkenes

Xiao‐Feng Wu, Yuanrui Wang, Ming Hou, Jiajun Zhang et al.
3 citations
Chemistry - A European Journal
Radical Photochemical Reactions
0.75
article

Carbon Monoxide and Alkoxycarbonyl Radical Enabled Migration Strategy for the Carbonylative Functionalization of Unactivated Alkenes

Xiao‐Feng Wu, Yuanrui Wang, Ming Hou, Jiajun Zhang, Hefei Yang
article en
3 citations

Abstract

Herein we report a "carbonylative migration" strategy for the acylation-esterification type double functionalization of unactivated alkenes using alkyloxalkyl chlorides and CO as the reagents. The transformation is proceeded by the alkoxycarbonyl radical addition to unactivated alkenes, followed by the insertion of carbon monoxide to induce intramolecular migration of heteroaryl groups, which is different from the traditional reaction modes. The reaction conditions were mild and well tolerated with varieties of functional groups. A variety of 1,4-dicarbonyl compounds with different ester groups were produced easily which has high potential applications in biology, medicine, and other fields.

Chemistry - A European JournalVol. 31(9)
Albert Einstein College of Medicine (US), Dalian Institute of Chemical Physics (CN), Chinese Academy of Sciences (CN), Leibniz Institute for Catalysis (DE), Dalian National Laboratory for Clean Energy (CN)
Dalian Institute of Chemical Physics
Openalex Percentile: Top 31%
Radical Photochemical Reactions
0.75
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Carbon Monoxide and Alkoxycarbonyl Radical Enabled Migration Strategy for the Carbonylative Functionalization of Unactivated Alkenes — Xiao‐Feng Wu, Yuanrui Wang, et al. · Chemistry - A European Journal (2024) | TGRS Research Map | TGRS