Issue 4, 2023

Photoredox-catalyzed intermolecular azidosulfonylation of alkenes with DABCO·(SO2)2, trimethylsilyl azide and thianthrenium salts

Abstract

A photoredox-catalyzed four-component reaction of alkenes, DABCO·(SO2)2, trimethylsilyl azide and alkyl thianthrenium salts is described, providing a facile route to β-azidosulfones in moderate to good yields with excellent regioselectivity under mild conditions. The thianthrenium salts serving as general precursors of unstable alkyl radicals enable the synthesis of β-azido alkylsulfones with diversity and efficiency. Additionally, this protocol can be further extended to other nucleophiles for the construction of different β-functionalized sulfones. Moreover, the installed azide group can be easily converted to free amino and other valuable groups.

Graphical abstract: Photoredox-catalyzed intermolecular azidosulfonylation of alkenes with DABCO·(SO2)2, trimethylsilyl azide and thianthrenium salts

Supplementary files

Article information

Article type
Research Article
Submitted
27 10 2022
Accepted
20 12 2022
First published
21 12 2022

Org. Chem. Front., 2023,10, 866-871

Photoredox-catalyzed intermolecular azidosulfonylation of alkenes with DABCO·(SO2)2, trimethylsilyl azide and thianthrenium salts

H. Ma, Y. Li, P. Wang, J. Ye, J. Zhang, G. Liu and J. Wu, Org. Chem. Front., 2023, 10, 866 DOI: 10.1039/D2QO01706G

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