Issue 4, 2022

An iron-catalyzed multicomponent reaction of cycloketone oxime esters, alkenes, DABCO·(SO2)2 and trimethylsilyl azide

Abstract

An iron-catalyzed four-component reaction of cycloketone oxime esters, alkenes, DABCO·(SO2)2 and trimethylsilyl azide (TMSN3) is described. This multicomponent radical transformation presents excellent regio- and chemoselectivity, leading to a range of β-azidosulfones in moderate to excellent yields. In this protocol, the utilization of a sulfur dioxide surrogate of DABCO·(SO2)2 as the source of the sulfonyl group enables the reaction to proceed efficiently under mild conditions without the need for strong oxidants. Additionally, the products can be transformed into β-aminosulfones and other valuable sulfonyl-containing nitrogen heterocycles.

Graphical abstract: An iron-catalyzed multicomponent reaction of cycloketone oxime esters, alkenes, DABCO·(SO2)2 and trimethylsilyl azide

Supplementary files

Article information

Article type
Research Article
Submitted
10 dec 2021
Accepted
31 dec 2021
First published
04 jan 2022

Org. Chem. Front., 2022,9, 917-922

An iron-catalyzed multicomponent reaction of cycloketone oxime esters, alkenes, DABCO·(SO2)2 and trimethylsilyl azide

J. Zhang, J. Wu, X. Chang, P. Wang, J. Xia and J. Wu, Org. Chem. Front., 2022, 9, 917 DOI: 10.1039/D1QO01842F

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