Intermolecular Trapping of Alkoxyl Radicals with Alkenes: A New Route to Ether Synthesis

Anne-Laure Barthelemy; Béatrice Tuccio; Emmanuel Magnier; Guillaume Dagousset

doi:10.1055/s-0037-1611785

Synlett, Table of Contents

Synlett 2019; 30(13): 1489-1495
DOI: 10.1055/s-0037-1611785

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Intermolecular Trapping of Alkoxyl Radicals with Alkenes: A New Route to Ether Synthesis

Anne-Laure Barthelemy

^aInstitut Lavoisier de Versailles, UMR 8180, Université de Versailles Saint-Quentin, 78035 Versailles Cedex, France Email: guillaume.dagousset@uvsq.fr

,

Béatrice Tuccio

^bAix-Marseille Université - CNRS, Institut de Chimie Radicalaire UMR 7273, F-13397 Marseille Cedex 20, France

,

Emmanuel Magnier

^aInstitut Lavoisier de Versailles, UMR 8180, Université de Versailles Saint-Quentin, 78035 Versailles Cedex, France Email: guillaume.dagousset@uvsq.fr

,

Guillaume Dagousset *

^aInstitut Lavoisier de Versailles, UMR 8180, Université de Versailles Saint-Quentin, 78035 Versailles Cedex, France Email: guillaume.dagousset@uvsq.fr

› Author Affiliations

Abstract

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Abstract

Alkoxyl radicals are highly reactive species which rapidly react by hydrogen atom transfer (HAT) or β-fragmentation to afford a carbon-centered radical. We discuss herein how these RO· radicals can be efficiently trapped in an intermolecular manner by styrene derivatives when they are generated by photoredox catalysis from the corresponding N-alkoxypyridinium salts. This allows for the synthesis of valuable ethers with complete anti-Markovnikov regioselectivity.

1 Introduction

2 Anti-Markovnikov Alkoxylation of Alkenes: Background

3 Addition of Alkoxyl Radicals to Styrenes

4 Summary and Outlook

Key words

ether synthesis - photoredox catalysis - alkoxyl radicals - anti-Markovnikov addition - alkenes - N-alkoxypyridinium

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References

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