PhIO/Et3N ⋅ 3HF‐Mediated Formation of Fluorinated 2H‐Azirines via Domino Fluorination/Azirination Reaction of Enamines. Issue 11 (14th April 2018)

• Record Type: Journal Article
• Authors: Zhang, Yong; Zhao, Xiaoyuan; Zhuang, Chen; Wang, Senlin; Zhang‐Negrerie, Daisy; Du, Yunfei
• Is Part Of: Advanced synthesis & catalysis. Volume 360:Issue 11(2018)
• Page Start: 2107
• Page End: 2112
• Publication Date: 2018-04-14
• Subjects: enamine -- difluoroiodoarene generated in situ -- domino reaction -- fluorination -- azirination; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.201800124
• Languages: English
• ISSNs: 1615-4150

Abstract

Abstract: A variety of enamine carboxylic esters and enaminones were converted to the biologically interesting fluorinated 2 H ‐azirines through reactions with PhIF2 generated in situ by PhIO and Et3 N ⋅ 3HF in 1, 2‐dichroloethane, which features the hypervalent iodine reagents‐mediated introduction of fluorine atom and formation of the 2 H ‐azirine skeleton under metal‐free conditions. The domino reaction is postulated to proceed via a PhIF2 ‐mediated oxidative fluorination and a subsequent azirination of the fluorinated enamine intermediates. Abstract :