Metal‐Free Visible‐Light‐Induced Atom‐Transfer Radical Addition Reaction of Alkenes/Alkynes with ICH2CN

Comprehensive Summary New blue‐light promoted methods for the addition of iodoacetonitrile (ICH2CN) to alkene/alkynes have been developed. The reaction led to the formation of cyanoalkylated products when conjugated alkene/styrene was used. In the case of alkynes and non‐conjugated alkenes, iodoalky...

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Bibliographic Details
Published in:Chinese journal of chemistry 2022-09, Vol.40 (17), p.2040-2046
Main Authors: Pan, Chunxiang, Meng, Yunyan, Deng, Yao, Zhou, Bingjie, Chen, Jingchao, He, Zhenxiu, Sun, Weiqing, Khan, Ruhima, Fan, Baomin
Format: Article
Language:English
Subjects:
Alkenes
Alkynes
Blue LED
Carboiodination
Cyanoalkylation
Iodides
Photochemistry
Reaction mechanisms
Styrene
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Summary:Comprehensive Summary New blue‐light promoted methods for the addition of iodoacetonitrile (ICH2CN) to alkene/alkynes have been developed. The reaction led to the formation of cyanoalkylated products when conjugated alkene/styrene was used. In the case of alkynes and non‐conjugated alkenes, iodoalkylation takes place furnishing the corresponding alkenyl iodides and alkyl iodides, respectively. Notably, trans‐alkenyl iodides were obtained as the major product. A plausible reaction mechanism is also proposed. A new method for the visible light induced addition of iodoacetonitrile (ICH2CN) to alkenes/alkynes has been demonstrated. Conjugated alkene/styrene gave cyanoalkylated products, alkynes furnished the iodoalkylation products and non‐conjugated alkenes gave alkyl iodides.
ISSN:1001-604X
1614-7065
DOI:10.1002/cjoc.202200144