Metal‐Free Visible‐Light‐Induced Atom‐Transfer Radical Addition Reaction of Alkenes/Alkynes with ICH2CN. Issue 17 (21st June 2022)

• Record Type: Journal Article
• Authors: Pan, Chunxiang; Meng, Yunyan; Deng, Yao; Zhou, Bingjie; Chen, Jingchao; He, Zhenxiu; Sun, Weiqing; Khan, Ruhima; Fan, Baomin
• Is Part Of: Chinese journal of chemistry. Volume 40:Issue 17(2022)
• Page Start: 2040
• Page End: 2046
• Publication Date: 2022-06-21
• Subjects: Blue LED -- Photochemistry -- Alkenes -- Alkynes -- Cyanoalkylation -- Carboiodination; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/cjoc.202200144
• Languages: English
• ISSNs: 1001-604X

Abstract

Comprehensive Summary: New blue‐light promoted methods for the addition of iodoacetonitrile (ICH2 CN) 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. Abstract : A new method for the visible light induced addition of iodoacetonitrile (ICH2 CN) to alkenes/alkynes has been demonstrated. Conjugated alkene/styrene gave cyanoalkylated products, alkynes furnished the iodoalkylation products and non‐conjugated alkenes gave alkyl iodides.