Visible-light Promoted Atom Transfer Radical Addition-Elimination (ATRE) Reaction for the Synthesis of Fluoroalkylated Alkenes Using DMA as Electron-Donor.

Wen-Wen Xu,Jiwei Gu,Xiao-Fei Li,Ting Mao,Le Wang,Chun-Yang He

doi:10.3390/molecules25030508

Abstract

Here, we describe a mild, catalyst-free and operationally-simple strategy for the direct fluoroalkylation of olefins driven by the photochemical activity of an electron donor−acceptor (EDA) complex between DMA and fluoroalkyl iodides. The significant advantages of this photochemical transformation are high efficiency, excellent functional group tolerance, and synthetic simplicity, thus providing a facile route for further application in pharmaceuticals and life sciences.

Highlights

Owing to their tendency to alter the lipophilicity, metabolic stability, and electronic properties of organic molecules, fluorinated organic compounds have been widely used in medicinal chemistry, and material sciences [1–9]
Alkenes play a ubiquitous role in the realm of chemical synthesis due to their enriched reactivity and abundance, fluoroalkylation of carbon-carbon double bonds is an attractive method for accessing fluorine containing compounds
We demonstrate a mild, catalyst-free and the photochemical activity of electron donor−acceptor (EDA) complex between DMA and fluoroalkyl operationally-simple strategy for the direct fluoroalkylation of olefins driven by the photochemical iodides

Summary

Introduction

Owing to their tendency to alter the lipophilicity, metabolic stability, and electronic properties of organic molecules, fluorinated organic compounds have been widely used in medicinal chemistry, and material sciences [1–9]. The development of safer, less toxic and more selective methods to introduce fluorinated functional groups into organic molecules has become an intensive topic of synthetic organic chemistry [10–19]. Alkenes play a ubiquitous role in the realm of chemical synthesis due to their enriched reactivity and abundance, fluoroalkylation of carbon-carbon double bonds is an attractive method for accessing fluorine containing compounds. The preparation of alkenes containing fluorinated functional groups via Heck-type reaction were less studied owning to the lack of efficient and general strategies [30–32]. Non-covalent interaction initiated fluoroalkylation reaction has emerged as an attractive strategy [37–47]. We demonstrate a Molecules 2020, 25, 508; doi:10.3390/molecules25030508 www.mdpi.com/journal/molecules

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Conclusion