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Synlett 2019; 30(13): 1489-1495
DOI: 10.1055/s-0037-1611785
DOI: 10.1055/s-0037-1611785
synpacts
Intermolecular Trapping of Alkoxyl Radicals with Alkenes: A New Route to Ether Synthesis
Further Information
Publication History
Received: 19 February 2019
Accepted after revision: 14 March 2019
Publication Date:
16 April 2019 (online)
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
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Examples of intermolecular addition of alkoxyl radicals onto alkenes:
Selected reviews on photoredox catalysis:
For reviews on photoredox-catalyzed generation of alkoxyl radicals, see:
For the formation of alkoxyl radicals under photoredox catalysis, see:
For a recent review, see:
Selected reviews:
Selected examples: