Issue 13, 2021

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

Abstract

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.

Graphical abstract: Synthesis of quaternary centres by single electron reduction and alkylation of alkylsulfones

Supplementary files

Article information

Article type
Edge Article
Submitted
09 jan 2021
Accepted
01 feb 2021
First published
04 feb 2021
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2021,12, 4866-4871

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

M. Nambo, Y. Tahara, J. C.-H. Yim, D. Yokogawa and C. M. Crudden, Chem. Sci., 2021, 12, 4866 DOI: 10.1039/D1SC00133G

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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