Alcohol Etherification via Alkoxy Radicals Generated by Visible-Light Photoredox Catalysis

[Image: see text] 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(sp(3))–H and C(sp(2))–H bonds. This visible-light phot...

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Autores principales: Rivero, Alexandra R., Fodran, Peter, Ondrejková, Alica, Wallentin, Carl-Johan
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2020
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7653678/
https://www.ncbi.nlm.nih.gov/pubmed/33040526
http://dx.doi.org/10.1021/acs.orglett.0c03058
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author Rivero, Alexandra R.
Fodran, Peter
Ondrejková, Alica
Wallentin, Carl-Johan
author_facet Rivero, Alexandra R.
Fodran, Peter
Ondrejková, Alica
Wallentin, Carl-Johan
author_sort Rivero, Alexandra R.
collection PubMed
description [Image: see text] 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(sp(3))–H and C(sp(2))–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.
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spelling pubmed-76536782020-11-12 Alcohol Etherification via Alkoxy Radicals Generated by Visible-Light Photoredox Catalysis Rivero, Alexandra R. Fodran, Peter Ondrejková, Alica Wallentin, Carl-Johan Org Lett [Image: see text] 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(sp(3))–H and C(sp(2))–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. American Chemical Society 2020-10-12 2020-11-06 /pmc/articles/PMC7653678/ /pubmed/33040526 http://dx.doi.org/10.1021/acs.orglett.0c03058 Text en © 2020 American Chemical Society This is an open access article published under a Creative Commons Attribution (CC-BY) License (http://pubs.acs.org/page/policy/authorchoice_ccby_termsofuse.html) , which permits unrestricted use, distribution and reproduction in any medium, provided the author and source are cited.
spellingShingle Rivero, Alexandra R.
Fodran, Peter
Ondrejková, Alica
Wallentin, Carl-Johan
Alcohol Etherification via Alkoxy Radicals Generated by Visible-Light Photoredox Catalysis
title Alcohol Etherification via Alkoxy Radicals Generated by Visible-Light Photoredox Catalysis
title_full Alcohol Etherification via Alkoxy Radicals Generated by Visible-Light Photoredox Catalysis
title_fullStr Alcohol Etherification via Alkoxy Radicals Generated by Visible-Light Photoredox Catalysis
title_full_unstemmed Alcohol Etherification via Alkoxy Radicals Generated by Visible-Light Photoredox Catalysis
title_short Alcohol Etherification via Alkoxy Radicals Generated by Visible-Light Photoredox Catalysis
title_sort alcohol etherification via alkoxy radicals generated by visible-light photoredox catalysis
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7653678/
https://www.ncbi.nlm.nih.gov/pubmed/33040526
http://dx.doi.org/10.1021/acs.orglett.0c03058
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