Synthesis of quaternary centres by single electron reduction and alkylation of alkylsulfones

A new method for the generation of tertiary radicals through single electron reduction of alkylsulfones promoted by Zn and 1,10-phenanthroline has been developed. These radicals could be employed in the Giese reaction, affording structurally diverse quaternary products in good yields. With the high...

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Detalles Bibliográficos
Autores principales: Nambo, Masakazu, Tahara, Yasuyo, Yim, Jacky C.-H., Yokogawa, Daisuke, Crudden, Cathleen M.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2021
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8179647/
https://www.ncbi.nlm.nih.gov/pubmed/34168761
http://dx.doi.org/10.1039/d1sc00133g
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author Nambo, Masakazu
Tahara, Yasuyo
Yim, Jacky C.-H.
Yokogawa, Daisuke
Crudden, Cathleen M.
author_facet Nambo, Masakazu
Tahara, Yasuyo
Yim, Jacky C.-H.
Yokogawa, Daisuke
Crudden, Cathleen M.
author_sort Nambo, Masakazu
collection PubMed
description A new method for the generation of tertiary radicals through single electron reduction of alkylsulfones promoted by Zn and 1,10-phenanthroline has been developed. These radicals could be employed in the Giese reaction, affording structurally diverse quaternary products in good yields. With the high modularity and functional group compatibility of sulfones, the utility of this method was demonstrated by intramolecular and iterative reactions to give complex structures. The radical generation process was investigated by control experiments and theoretical calculations.
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spelling pubmed-81796472021-06-23 Synthesis of quaternary centres by single electron reduction and alkylation of alkylsulfones Nambo, Masakazu Tahara, Yasuyo Yim, Jacky C.-H. Yokogawa, Daisuke Crudden, Cathleen M. Chem Sci Chemistry A new method for the generation of tertiary radicals through single electron reduction of alkylsulfones promoted by Zn and 1,10-phenanthroline has been developed. These radicals could be employed in the Giese reaction, affording structurally diverse quaternary products in good yields. With the high modularity and functional group compatibility of sulfones, the utility of this method was demonstrated by intramolecular and iterative reactions to give complex structures. The radical generation process was investigated by control experiments and theoretical calculations. The Royal Society of Chemistry 2021-02-04 /pmc/articles/PMC8179647/ /pubmed/34168761 http://dx.doi.org/10.1039/d1sc00133g Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by/3.0/
spellingShingle Chemistry
Nambo, Masakazu
Tahara, Yasuyo
Yim, Jacky C.-H.
Yokogawa, Daisuke
Crudden, Cathleen M.
Synthesis of quaternary centres by single electron reduction and alkylation of alkylsulfones
title Synthesis of quaternary centres by single electron reduction and alkylation of alkylsulfones
title_full Synthesis of quaternary centres by single electron reduction and alkylation of alkylsulfones
title_fullStr Synthesis of quaternary centres by single electron reduction and alkylation of alkylsulfones
title_full_unstemmed Synthesis of quaternary centres by single electron reduction and alkylation of alkylsulfones
title_short Synthesis of quaternary centres by single electron reduction and alkylation of alkylsulfones
title_sort synthesis of quaternary centres by single electron reduction and alkylation of alkylsulfones
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8179647/
https://www.ncbi.nlm.nih.gov/pubmed/34168761
http://dx.doi.org/10.1039/d1sc00133g
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AT yokogawadaisuke synthesisofquaternarycentresbysingleelectronreductionandalkylationofalkylsulfones
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