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Issue 16, 2019
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Desulfonative photoredox alkylation of N-heteroaryl sulfones – an acid-free approach for substituted heteroarene synthesis

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Abstract

Minisci-type alkylation of electron-deficient heteroarenes has been a pivotal technique for medicinal chemists in the synthesis of drug-like molecules. However, such transformations usually require harsh conditions (e.g., strong acids, stoichiometric amount of oxidants, elevated temperatures, etc.). Herein, by utilizing photoredox catalysis, a highly-selective alkylation method using heteroaryl sulfones has been developed that can be carried out under acid-free and redox-neutral conditions. Because of these mild conditions, challenging yet privileged structures, such as monosaccharides and unprotected secondary amines, can be installed.

Graphical abstract: Desulfonative photoredox alkylation of N-heteroaryl sulfones – an acid-free approach for substituted heteroarene synthesis

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Article information


Submitted
14 Feb 2019
Accepted
14 Mar 2019
First published
14 Mar 2019

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2019,10, 4389-4393
Article type
Edge Article

Desulfonative photoredox alkylation of N-heteroaryl sulfones – an acid-free approach for substituted heteroarene synthesis

Z. Wang, S. Zheng, J. K. Matsui, Z. Lu and G. A. Molander, Chem. Sci., 2019, 10, 4389
DOI: 10.1039/C9SC00776H

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