Issue 7, 2023

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

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 α-sp3 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 tBuONa or KOH, which promote homolysis of perfluoroalkyl iodides under mild conditions.

Graphical abstract: 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

Supplementary files

Article information

Article type
Edge Article
Submitted
07 Nov 2022
Accepted
29 Dec 2022
First published
24 Jan 2023
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2023,14, 1732-1741

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

Y. Wang, Z. Cao, Q. He, X. Huang, J. Liu, H. Neumann, G. Chen and M. Beller, Chem. Sci., 2023, 14, 1732 DOI: 10.1039/D2SC06145G

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