Wacker-type oxidation of styrenes with Markovnikov selectivity using copper as a site-selective sequential photooxidant-photoreductant

Abderrazak, Youssef and Chinchole, Anurag and Reiser, Oliver (2024) Wacker-type oxidation of styrenes with Markovnikov selectivity using copper as a site-selective sequential photooxidant-photoreductant. CATALYSIS SCIENCE & TECHNOLOGY, 14 (14). pp. 4068-4074. ISSN 2044-4753, 2044-4761

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Abstract

We report a palladium-free Wacker-type oxidation of styrenes using CuCl2/KBr as the catalyst and trichloroisocyanuric acid as a stoichiometric chlorine radical source. The reaction protocol is compatible with diverse functional groups, affording selectively acetophenones. The mechanistic analysis revealed that a site-selective sequential CuII-photooxidation/CuI-photoreduction of the intermediary chlorohydrin is the key to the success of this transformation. Copper acts as a site-selective photooxidant and photoreductant, thus enabling the Wacker-type oxidation of styrenes to acetophenones.

Item Type: Article
Uncontrolled Keywords: PHOTOCHEMISTRY; ACIDS;
Subjects: 500 Science > 540 Chemistry & allied sciences
Divisions: Chemistry and Pharmacy > Institut für Organische Chemie
Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Oliver Reiser
Depositing User: Dr. Gernot Deinzer
Date Deposited: 25 Jul 2025 08:15
Last Modified: 25 Jul 2025 08:15
URI: https://pred.uni-regensburg.de/id/eprint/63757

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