Related Experiment Video
Updated: Aug 22, 2025

Efficient Synthesis of Polyfunctionalized Benzenes in Water via Persulfate-promoted Benzannulation of α,β-Unsaturated Compounds and Alkynes
Published on: December 16, 2019
Visible-Light-Mediated Radical Silyl-Oximation of Activated Alkenes Using tert-Butyl Nitrite and Silanes
Stefanie Plöger1, Armido Studer1
1Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, 48149 Münster, Germany.
Abstract:
A metal-free radical 1,2-difunctionalization of activated alkenes with various silanes and tert-butyl nitrite is reported. The radical cascade occurs by light-promoted homolytic O-NO bond cleavage of tert-butyl nitrite and subsequent hydrogen atom abstraction by the alkoxyl radical from the silane. Silyl radical addition to the alkene and highly selective cross-coupling of the NO radical with the Si-adduct C-radical provide the silyl-oximation product in moderate to good yields. The reaction features good functional group tolerance and is easily scaled up.
More Related Videos
Related Concept Videos
Radical Reactivity: Nucleophilic Radicals
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide
Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride
The bonds formed in this reaction are stronger than the bonds broken, making it energetically favorable. The reaction follows a radical chain mechanism similar to radical halogenation...
Radical Reactivity: Concentration Effects
Radical Substitution: Allylic Bromination
Radical Anti-Markovnikov Addition to Alkenes: Overview

