Abstract
A mechanistically divergent method is described that, employing a commercially available hypervalent iodine(III) reagent, generates alkoxy radicals from 1°, 2°, and 3° alcohols and allows their use in the functionalization of C(sp3)–H and C(sp2)–H bonds. This visible-light photoredox catalysis produces alkyl ethers via 1,5/6-hydrogen atom transfer or aryl ethers via 1,5-addition. This mild methodology provides a practical strategy for the synthesis of acetals, orthoesters, tetrahydrofurans, and chromanes.
Highlights
A mechanistically divergent method is described that, employing a commercially available hypervalent iodine(III) reagent, generates alkoxy radicals from 1°, 2°, and 3° alcohols and allows their use in the functionalization of C(sp3)−H and C(sp2)− H bonds
Transition-metal catalysis became a heavily utilized tool for the synthesis of ethers, overcoming the functional group incompatibility observed for more classical methods.[3]
Photoredox catalysis has recently emerged as a powerful alternative that allows for direct C−O coupling using milder conditions.[5]
Summary
Carl-Johan Wallentin − Department of Chemistry and Molecular Biology, University of Gothenburg, 412 96. Rivero − Department of Chemistry and Molecular Biology, University of Gothenburg, 412 96 Gothenburg, Sweden. Peter Fodran − Department of Chemistry and Molecular Biology, University of Gothenburg, 412 96 Gothenburg, Sweden. Alica Ondrejková − Department of Chemistry and Molecular Biology, University of Gothenburg, 412 96 Gothenburg, Sweden; orcid.org/0000-0001-7806-5064.
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