Catalytic Wacker‐type Oxidations Using Visible Light Photoredox Catalysis

A combined palladium/photoredox catalytic system for the efficient oxidation of terminal olefins to the corresponding methyl ketones is presented. The interplay of air, water, and light leads to a protocol in which the stoichiometric oxidants required for oxidative palladium catalysis are substitute...

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Bibliographic Details
Published inChemCatChem Vol. 11; no. 7; pp. 1889 - 1892
Main Authors Ho, Yee Ann, Paffenholz, Eva, Kim, Hyun Jin, Orgis, Benjamin, Rueping, Magnus, Fabry, David C.
Format Journal Article
LanguageEnglish
Published Weinheim Wiley Subscription Services, Inc 04.04.2019
Subjects
Alkenes
Catalysis
Copper-free
Electron transfer
Ketone
Ketones
Oxidation
Oxidizing agents
Palladium
Photoredox catalysis
Substrates
Superoxide
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Summary:A combined palladium/photoredox catalytic system for the efficient oxidation of terminal olefins to the corresponding methyl ketones is presented. The interplay of air, water, and light leads to a protocol in which the stoichiometric oxidants required for oxidative palladium catalysis are substituted with catalytic, single‐electron transfer processes. Detailed mechanistic investigations revealed the role of the key components, in situ generated species, and catalysts. A broad range of substrates was examined in homogeneous as well as heterogeneous photoredox protocols, delivering the desired products in good yields. A combined palladium/photoredox catalytic system for the efficient oxidation of terminal olefins to the corresponding methyl ketones is presented. The interplay of air, water, and light leads to a protocol in which the stoichiometric oxidants required for oxidative palladium catalysis are substituted with catalytic, single‐electron transfer processes.
ISSN:1867-3880
1867-3899
DOI:10.1002/cctc.201900271