Photocatalytic Functionalization of Perfluoroalkyl Alkenyl Iodides via Vinyl Radicals: Synthesis of Perfluoroalkylated Naphthalenes

Organic Letters 2026

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Authors: Shuang Liu, Ke Zhou, Yu-Jie Zhou, Mengtao Ma, Xian-Xian Mao, Zhi-Liang Shen, Xue‐Qiang Chu
DOI: 10.1021/acs.orglett.6c01318
Cited by: 4
References: 46

Abstract

A photocatalytic [4 + 2] cycloaddition of perfluoroalkyl alkenyl iodides with 1,1-di(hetero)aryl alkenes was developed for the modular synthesis of multisubstituted naphthalenes. Through a key perfluoroalkylated vinyl radical intermediate that undergoes a sequence of intermolecular addition, Mallory-type cyclization, and dehydrogenative aromatization, the method enables the precise incorporation of diverse perfluoroalkyl moieties onto carbocycles. Interestingly, perfluoroalkyl alkenyl iodides exhibit distinct radical reactivity and selectivity features mainly originating from the structural and electronic attributes of the attached perfluoroalkyl group.

Fields of Study & Subjects

Fluorine in Organic Chemistry Radical Photochemical Reactions Inorganic Fluorides and Related Compounds

Publication details

Journal / source
Organic Letters
Publisher
American Chemical Society (ACS)
Volume
28
Issue
18
Pages
5810–5815
Publication date
24 April 2026
Language
EN