Electrochemical Benzylic C(sp(3))–H Acyloxylation

[Image: see text] The development of sustainable C(sp(3))–H functionalization methods is of great interest to the pharmaceutical and agrochemical industries. Anodic oxidation is an efficient means of producing benzylic cations that can undergo subsequent in situ nucleophilic attack to afford functio...

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Autores principales: Atkins, Alexander P., Rowett, Albert C., Heard, David M., Tate, Joseph A., Lennox, Alastair J. J.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9315976/
https://www.ncbi.nlm.nih.gov/pubmed/35829756
http://dx.doi.org/10.1021/acs.orglett.2c01930
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author Atkins, Alexander P.
Rowett, Albert C.
Heard, David M.
Tate, Joseph A.
Lennox, Alastair J. J.
author_facet Atkins, Alexander P.
Rowett, Albert C.
Heard, David M.
Tate, Joseph A.
Lennox, Alastair J. J.
author_sort Atkins, Alexander P.
collection PubMed
description [Image: see text] The development of sustainable C(sp(3))–H functionalization methods is of great interest to the pharmaceutical and agrochemical industries. Anodic oxidation is an efficient means of producing benzylic cations that can undergo subsequent in situ nucleophilic attack to afford functionalized benzylic products. Herein, we demonstrate the suitability of carboxylic acids as nucleophiles to yield benzylic esters. This method employs a series of secondary benzylic substrates and functionalized carboxylic acids and is demonstrated on a gram scale in flow.
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spelling pubmed-93159762022-07-27 Electrochemical Benzylic C(sp(3))–H Acyloxylation Atkins, Alexander P. Rowett, Albert C. Heard, David M. Tate, Joseph A. Lennox, Alastair J. J. Org Lett [Image: see text] The development of sustainable C(sp(3))–H functionalization methods is of great interest to the pharmaceutical and agrochemical industries. Anodic oxidation is an efficient means of producing benzylic cations that can undergo subsequent in situ nucleophilic attack to afford functionalized benzylic products. Herein, we demonstrate the suitability of carboxylic acids as nucleophiles to yield benzylic esters. This method employs a series of secondary benzylic substrates and functionalized carboxylic acids and is demonstrated on a gram scale in flow. American Chemical Society 2022-07-13 2022-07-22 /pmc/articles/PMC9315976/ /pubmed/35829756 http://dx.doi.org/10.1021/acs.orglett.2c01930 Text en © 2022 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Atkins, Alexander P.
Rowett, Albert C.
Heard, David M.
Tate, Joseph A.
Lennox, Alastair J. J.
Electrochemical Benzylic C(sp(3))–H Acyloxylation
title Electrochemical Benzylic C(sp(3))–H Acyloxylation
title_full Electrochemical Benzylic C(sp(3))–H Acyloxylation
title_fullStr Electrochemical Benzylic C(sp(3))–H Acyloxylation
title_full_unstemmed Electrochemical Benzylic C(sp(3))–H Acyloxylation
title_short Electrochemical Benzylic C(sp(3))–H Acyloxylation
title_sort electrochemical benzylic c(sp(3))–h acyloxylation
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9315976/
https://www.ncbi.nlm.nih.gov/pubmed/35829756
http://dx.doi.org/10.1021/acs.orglett.2c01930
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AT lennoxalastairjj electrochemicalbenzyliccsp3hacyloxylation

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