Issue 14, 2024

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

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.

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

Supplementary files

Article information

Article type
Paper
Submitted
07 May 2024
Accepted
13 Jun 2024
First published
14 Jun 2024

Catal. Sci. Technol., 2024,14, 4068-4074

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

Y. Abderrazak, A. Chinchole and O. Reiser, Catal. Sci. Technol., 2024, 14, 4068 DOI: 10.1039/D4CY00590B

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