Related Experiment Video
Updated: Aug 16, 2026

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
Radical Relay Meets Migration: TBADT-Catalyzed Access to 3,3-Disubstituted Oxindoles via Alkyl/Aryl Shift
Punith S Gowda1, Jagadeesh Reddy Thondur1, Duddu S Sharada2
1Department of Chemistry, Indian Institute of Technology Hyderabad, Kandi, Sangareddy, Telangana502284, India.
Abstract:
Herein, we report a hitherto unexplored light-induced radical cascade process for the synthesis of oxindole frameworks using tetrabutylammonium decatungstate (TBADT), a well-known hydrogen-atom-transfer (HAT) photocatalyst. This cascade photochemical transformation proceeds via an unprecedented intermolecular radical addition, an intramolecular ring closure, and a 1,2-alkyl/aryl shift. Notably, this process is highly atom-economic; the initial acyl C-H activation is feasible under mild conditions without the use of additives or external reagents. The strategy is compatible with various aldehydes and diverse N-(2-ethynylaryl)amides, delivering structurally diverse 3,3-disubstituted oxindoles, including structurally diverse drug derivatives and other synthetic extensions.
More Related Videos
10:42Preparation of N-(2-alkoxyvinyl)sulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
Published on: January 3, 2018
06:34Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)
Published on: June 20, 2014
Related Concept Videos
Radical Substitution: Allylic Bromination
Radical Substitution: Halogenation of Alkanes and Alkyl Substituents
In the initiation step of the reaction, the chlorine molecule undergoes homolytic cleavage in the presence of light or heat, forming two highly reactive chlorine radicals. Propagation occurs in two...
Radical Substitution: Allylic Chlorination
Radical Reactivity: Nucleophilic Radicals
Radical Anti-Markovnikov Addition to Alkenes: Overview
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 reactions,...