Visible-light-promoted nitrone synthesis from nitrosoarenes under catalyst- and additive-free conditions

Abstract

A green and sustainable nitrone formation reaction via visible-light-promoted reaction of aryl diazoacetates with nitrosoarenes is described. This protocol exhibits good functional group tolerance and broad substrate scope for both aryl diazoacetates with nitrosoarenes. Comparing the reported methods for the synthesis of nitrones from nitrosoarenes, the reaction described herein occurs under sole visible-light irradiation without the need of any catalysts and additives.

Visible-Light-Initiated Multicomponent Reactions of α-Diazoesters to Access Organophosphorus Compounds

“…As clean and sustainable energy, visible light has been widely applied to promote various types of organic reactions. , In particular, visible-light-induced carbene transfer reactions of diazo compounds have been developed as an attractive and efficient protocol for the rapid assemble of the densely functionalized molecules via free carbene intermediates due to their mild and metal-free advantages. , In 2022, Yang and Zhou presented a visible-light-mediated aerobic oxyphosphorylation of α-diazoesters and H-phosphine oxides to access α-phosphoryloxy carbonyl compounds (Scheme d) . Since Szabó and Koenigs independently reported metal-catalyzed and photochemical ring opening of cyclic ethers with diazo compounds and N -fluorobenzenesulfonimide, multicomponent reactions of aryldiazoacetates, cyclic ethers, and nucleophiles have attracted great attention of chemists in synthetic community .…”

Synthesis and Characterization of Some New Nitrones Derivatives and Screening their Biological Activities

“…These substances are also important synthetic intermediates. Several nitrones have been found as essential components in the structure of important drugs (Cai et al, 2021;Salman & Majeed, 2013;Thakur et al, 2021). These compounds have an important role in trapping free radicals in the body (Besson et al, 2019;Deletraz et al, 2020;Floyd et al, 2002;Janzen & Blackburn, 1968;Jung et al, 2021).…”

Metal-free visible-light-induced multi-component reactions of α-diazoesters leading to S-alkyl dithiocarbamates

“…20 Among the various synthetic transformations, visible-light-promoted carbene transfer reactions of α-diazo compounds have been developed as a powerful protocol for the synthesis of various densely functionalized molecules. 21,22 In comparison with metal-mediated carbene transfer reactions, photochemical transformations of α-diazo compounds using visible light as the sole energy source could be conducted under milder and greener conditions without the exclusion of moisture or air. 23 In continuation of our interest in photochemical reactions, 24 herein, we wish to report a metal-free and visible-light-mediated protocol for the synthesis of S -alkyl dithiocarbamates from α-diazoesters, amines and CS 2 at room temperature under air, in which nitrogen was generated as the sole side-product (Scheme 1c).…”