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

Yaxin Wang, Zehui Cao, Qin He, Xin Huang, Jiaxi Liu, Helfried Neumann, Gong Chen, Matthias Beller

Research output: Contribution to journalArticlepeer-review

5 Scopus citations

Abstract

A simple, efficient, and convenient activation of perfluoroalkyl iodides by tBuONa or KOH, without expensive photo- or transition metal catalysts, allows the promotion of versatile a-sp3 C-H amidation reactions of alkyl ethers and benzylic hydrocarbons, C-H iodination of heteroaryl compounds, and perfluoroalkylations of electron-rich p bonds. Mechanistic studies show that these novel protocols are based on the halogen bond interaction between perfluoroalkyl iodides and tBuONa or KOH, which promote homolysis of perfluoroalkyl iodides under mild conditions.

Original languageEnglish
Pages (from-to)1732-1741
Number of pages10
JournalChemical Science
Volume14
Issue number7
DOIs
StatePublished - 24 Jan 2023
Externally publishedYes

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