Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 59, Issue 8, Pages 3178-3183Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201913930
Keywords
C-H alkoxylation; electrocatalysis; electrochemistry; nickel; oxygenation
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Funding
- DFG (Gottfried-Wilhelm-Leibniz award)
- CSC
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Nickela-electrooxidative C-H alkoxylations with challenging secondary alcohols were accomplished in a fully dehydrogenative fashion, thereby avoiding stoichiometric chemical oxidants, with H-2 as the only stoichiometric byproduct. The nickela-electrocatalyzed oxygenation proved viable with various (hetero)arenes, including naturally occurring secondary alcohols, without racemization. Detailed mechanistic investigation, including DFT calculations and cyclovoltammetric studies of a well-defined C-H activated nickel(III) intermediate, suggest an oxidation-induced reductive elimination at nickel(III).
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