Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 137, Issue 25, Pages 8206-8218Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.5b03956
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Funding
- EPSRC
- University of Liverpool
- EPSRC [EP/K039687/1] Funding Source: UKRI
- Engineering and Physical Sciences Research Council [EP/K039687/1] Funding Source: researchfish
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A mild and operationally simple iron-catalyzed protocol for the selective aerobic oxidation of aromatic olefins to carbonyl compounds is described. Catalyzed by a Fe(III) species bearing a pyridine bisimidazoline ligand at 1 atm of O-2, alpha- and beta-substituted styrenes were cleaved to afford benzaldehydes and aromatic ketones generally in high yields with excellent chemoselectivity and very good functional group tolerance, including those containing radical-sensitive groups. With alpha-halo-substituted styrenes, the oxidation took place with concomitant halide migration to afford alpha-halo acetophenones. Various observations have been made, pointing to a mechanism in which both molecular oxygen and the olefinic substrate coordinate to the iron center, leading to the formation of a dioxetane intermediate, which collapses to give the carbonyl product.
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