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Electrochemical formal homocoupling of sec-alcohols

Electrochemical pinacol coupling of carbonyl compounds in an undivided cell with a sacrificial anode would be a promising approach toward synthetically valuable vic-1,2-diol scaffolds without using low-valent metal reductants. However, sacrificial anodes produce an equimolar amount of metal waste, w...

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Autores principales: Yamamoto, Kosuke, Arita, Kazuhisa, Shiota, Masashi, Kuriyama, Masami, Onomura, Osamu
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9443307/
https://www.ncbi.nlm.nih.gov/pubmed/36105731
http://dx.doi.org/10.3762/bjoc.18.108
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author Yamamoto, Kosuke
Arita, Kazuhisa
Shiota, Masashi
Kuriyama, Masami
Onomura, Osamu
author_facet Yamamoto, Kosuke
Arita, Kazuhisa
Shiota, Masashi
Kuriyama, Masami
Onomura, Osamu
author_sort Yamamoto, Kosuke
collection PubMed
description Electrochemical pinacol coupling of carbonyl compounds in an undivided cell with a sacrificial anode would be a promising approach toward synthetically valuable vic-1,2-diol scaffolds without using low-valent metal reductants. However, sacrificial anodes produce an equimolar amount of metal waste, which may be a major issue in terms of sustainable chemistry. Herein, we report a sacrificial anode-free electrochemical protocol for the synthesis of pinacol-type vic-1,2-diols from sec-alcohols, namely benzyl alcohol derivatives and ethyl lactate. The corresponding vic-1,2-diols are obtained in moderate to good yields, and good to high levels of stereoselectivity are observed for sec-benzyl alcohol derivatives. The present transformations smoothly proceed in a simple undivided cell under constant current conditions without the use of external chemical oxidants/reductants, and transition-metal catalysts.
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spelling pubmed-94433072022-09-13 Electrochemical formal homocoupling of sec-alcohols Yamamoto, Kosuke Arita, Kazuhisa Shiota, Masashi Kuriyama, Masami Onomura, Osamu Beilstein J Org Chem Letter Electrochemical pinacol coupling of carbonyl compounds in an undivided cell with a sacrificial anode would be a promising approach toward synthetically valuable vic-1,2-diol scaffolds without using low-valent metal reductants. However, sacrificial anodes produce an equimolar amount of metal waste, which may be a major issue in terms of sustainable chemistry. Herein, we report a sacrificial anode-free electrochemical protocol for the synthesis of pinacol-type vic-1,2-diols from sec-alcohols, namely benzyl alcohol derivatives and ethyl lactate. The corresponding vic-1,2-diols are obtained in moderate to good yields, and good to high levels of stereoselectivity are observed for sec-benzyl alcohol derivatives. The present transformations smoothly proceed in a simple undivided cell under constant current conditions without the use of external chemical oxidants/reductants, and transition-metal catalysts. Beilstein-Institut 2022-08-22 /pmc/articles/PMC9443307/ /pubmed/36105731 http://dx.doi.org/10.3762/bjoc.18.108 Text en Copyright © 2022, Yamamoto et al. https://creativecommons.org/licenses/by/4.0/This is an open access article licensed under the terms of the Beilstein-Institut Open Access License Agreement (https://www.beilstein-journals.org/bjoc/terms/terms), which is identical to the Creative Commons Attribution 4.0 International License (https://creativecommons.org/licenses/by/4.0 (https://creativecommons.org/licenses/by/4.0/) ). The reuse of material under this license requires that the author(s), source and license are credited. Third-party material in this article could be subject to other licenses (typically indicated in the credit line), and in this case, users are required to obtain permission from the license holder to reuse the material.
spellingShingle Letter
Yamamoto, Kosuke
Arita, Kazuhisa
Shiota, Masashi
Kuriyama, Masami
Onomura, Osamu
Electrochemical formal homocoupling of sec-alcohols
title Electrochemical formal homocoupling of sec-alcohols
title_full Electrochemical formal homocoupling of sec-alcohols
title_fullStr Electrochemical formal homocoupling of sec-alcohols
title_full_unstemmed Electrochemical formal homocoupling of sec-alcohols
title_short Electrochemical formal homocoupling of sec-alcohols
title_sort electrochemical formal homocoupling of sec-alcohols
topic Letter
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9443307/
https://www.ncbi.nlm.nih.gov/pubmed/36105731
http://dx.doi.org/10.3762/bjoc.18.108
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