Activation of perfluoroalkyl iodides by anions: extending the scope of halogen bond activation to C(sp3)–H amidation, C(sp2)–H iodination, and perfluoroalkylation reactions. Issue 7 (24th January 2023)

• Record Type: Journal Article
• Authors: Wang, Yaxin; Cao, Zehui; He, Qin; Huang, Xin; Liu, Jiaxi; Neumann, Helfried; Chen, Gong; Beller, Matthias
• Is Part Of: Chemical science. Volume 14:Issue 7(2023)
• Page Start: 1732
• Page End: 1741
• Publication Date: 2023-01-24
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/d2sc06145g
• Languages: English
• ISSNs: 2041-6520

Abstract

Abstract : A simple activation of perfluoroalkyl iodides by t BuONa or KOH allows the promotion of α-sp 3 C–H amidation reactions of alkyl ethers and benzylic hydrocarbons, C–H iodination of heteroaryl compounds, and perfluoroalkylations of electron-rich π bonds. Abstract : A simple, efficient, and convenient activation of perfluoroalkyl iodides by t BuONa or KOH, without expensive photo- or transition metal catalysts, allows the promotion of versatile α-sp 3 C–H amidation reactions of alkyl ethers and benzylic hydrocarbons, C–H iodination of heteroaryl compounds, and perfluoroalkylations of electron-rich π bonds. Mechanistic studies show that these novel protocols are based on the halogen bond interaction between perfluoroalkyl iodides and t BuONa or KOH, which promote homolysis of perfluoroalkyl iodides under mild conditions.