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Electrochemical Proton Reduction over Nickel Foam for Z‐Stereoselective Semihydrogenation/deuteration of Functionalized Alkynes

Selective reduction strategies based on abundant‐metal catalysts are very important in the production of chemicals. In this paper, a method for the electrochemical semihydrogenation and semideuteration of alkynes to form Z‐alkenes was developed, using a simple nickel foam as catalyst and H(3)O(+) or...

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Autores principales: Valiente, Alejandro, Martínez‐Pardo, Pablo, Kaur, Gurpreet, Johansson, Magnus J., Martín‐Matute, Belén
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2021
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9300003/
https://www.ncbi.nlm.nih.gov/pubmed/34738723
http://dx.doi.org/10.1002/cssc.202102221
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author Valiente, Alejandro
Martínez‐Pardo, Pablo
Kaur, Gurpreet
Johansson, Magnus J.
Martín‐Matute, Belén
author_facet Valiente, Alejandro
Martínez‐Pardo, Pablo
Kaur, Gurpreet
Johansson, Magnus J.
Martín‐Matute, Belén
author_sort Valiente, Alejandro
collection PubMed
description Selective reduction strategies based on abundant‐metal catalysts are very important in the production of chemicals. In this paper, a method for the electrochemical semihydrogenation and semideuteration of alkynes to form Z‐alkenes was developed, using a simple nickel foam as catalyst and H(3)O(+) or D(3)O(+) as sources of hydrogen or deuterium. Good yields and excellent stereoselectivities (Z/E up to 20 : 1) were obtained under very mild reaction conditions. The reaction proceeded with terminal and nonterminal alkynes, and also with alkynes containing easily reducible functional groups, such as carbonyl groups, as well as aryl chlorides, bromides, and even iodides. The nickel‐foam electrocatalyst could be recycled up to 14 times without any change in its catalytic properties.
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spelling pubmed-93000032022-07-21 Electrochemical Proton Reduction over Nickel Foam for Z‐Stereoselective Semihydrogenation/deuteration of Functionalized Alkynes Valiente, Alejandro Martínez‐Pardo, Pablo Kaur, Gurpreet Johansson, Magnus J. Martín‐Matute, Belén ChemSusChem Research Articles Selective reduction strategies based on abundant‐metal catalysts are very important in the production of chemicals. In this paper, a method for the electrochemical semihydrogenation and semideuteration of alkynes to form Z‐alkenes was developed, using a simple nickel foam as catalyst and H(3)O(+) or D(3)O(+) as sources of hydrogen or deuterium. Good yields and excellent stereoselectivities (Z/E up to 20 : 1) were obtained under very mild reaction conditions. The reaction proceeded with terminal and nonterminal alkynes, and also with alkynes containing easily reducible functional groups, such as carbonyl groups, as well as aryl chlorides, bromides, and even iodides. The nickel‐foam electrocatalyst could be recycled up to 14 times without any change in its catalytic properties. John Wiley and Sons Inc. 2021-12-16 2022-01-10 /pmc/articles/PMC9300003/ /pubmed/34738723 http://dx.doi.org/10.1002/cssc.202102221 Text en © 2021 The Authors. ChemSusChem published by Wiley-VCH GmbH https://creativecommons.org/licenses/by/4.0/This is an open access article under the terms of the http://creativecommons.org/licenses/by/4.0/ (https://creativecommons.org/licenses/by/4.0/) License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
spellingShingle Research Articles
Valiente, Alejandro
Martínez‐Pardo, Pablo
Kaur, Gurpreet
Johansson, Magnus J.
Martín‐Matute, Belén
Electrochemical Proton Reduction over Nickel Foam for Z‐Stereoselective Semihydrogenation/deuteration of Functionalized Alkynes
title Electrochemical Proton Reduction over Nickel Foam for Z‐Stereoselective Semihydrogenation/deuteration of Functionalized Alkynes
title_full Electrochemical Proton Reduction over Nickel Foam for Z‐Stereoselective Semihydrogenation/deuteration of Functionalized Alkynes
title_fullStr Electrochemical Proton Reduction over Nickel Foam for Z‐Stereoselective Semihydrogenation/deuteration of Functionalized Alkynes
title_full_unstemmed Electrochemical Proton Reduction over Nickel Foam for Z‐Stereoselective Semihydrogenation/deuteration of Functionalized Alkynes
title_short Electrochemical Proton Reduction over Nickel Foam for Z‐Stereoselective Semihydrogenation/deuteration of Functionalized Alkynes
title_sort electrochemical proton reduction over nickel foam for z‐stereoselective semihydrogenation/deuteration of functionalized alkynes
topic Research Articles
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9300003/
https://www.ncbi.nlm.nih.gov/pubmed/34738723
http://dx.doi.org/10.1002/cssc.202102221
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