Related Experiment Video
Updated: Feb 11, 2026

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Electron-Shuttle Catalysis by Diaryl Diselenides for Photochemical Anti-Markovnikov Hydroalkoxylation of Alkenes
Inho Jang1, Hun Young Kim2, Kyungsoo Oh1
1Center for Metareceptome Research, Graduate School of Pharmaceutical Sciences, Chung-Ang University, 84 Heukseok-ro, Dongjak, Seoul 06974, Republic of Korea.
Abstract:
The development of general anti-Markovnikov hydroalkoxylation methods remains challenging due to competing alkene oxidation and photocatalyst-alcohol compatibility issues. Herein, diaryl diselenides serve as efficient electron-shuttle catalysts for visible-light-driven anti-Markovnikov hydroalkoxylation in combination with TPT+BF4-. A broad range of aryl- and alkyl-substituted alkenes and diverse alcohols are accommodated, affording products up to 97% yield. Mechanistic studies reveal a diselenide-mediated, multistep electron-shuttle pathway that enables mild and selective transformations.
Related Concept Videos
Radical Anti-Markovnikov Addition to Alkenes: Mechanism
The mechanism starts with chain initiation, which involves two steps. In the first chain initiation step, a weak peroxide bond is homolytically cleaved upon mild heating to form two alkoxy radicals. In the second initiation step, a hydrogen atom is abstracted by the alkoxy...
Radical Anti-Markovnikov Addition to Alkenes: Overview
Radical Anti-Markovnikov Addition to Alkenes: Thermodynamics
Catalysis
Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule
The hydrohalogenation of an unsymmetrical alkene can yield two haloalkane products, depending on which vinylic carbon takes up the halogen. However, one product usually predominates, where hydrogen adds to the vinylic carbon bearing the...
Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids

