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- Title
2,2'‐Biquinoline‐Based Recyclable Electroauxiliaries for the Generation of Alkyl Radicals via C−C Bond Cleavage.
- Authors
Ratnam, Shahilan; Unone, Shreya; Janssen‐Müller, Daniel
- Abstract
Alkyl radical precursors are essential for a wide variety of photocatalytic and 3d‐metal‐catalyzed C−C bond forming reactions. Neutral organic heterocycles as electroauxiliaries such as 4‐alkyl Hantzsch esters have become reliable tools for alkyl radical formation. Here we show that 2,2'‐biquinoline‐derived alkyl‐substituted dihydroquinolines act as competent radical precursors with the ability to form primary, secondary and tertiary alkyl radicals. Hydroalkylation of benzalmalononitriles and N‐Boc protected diazenes has been achieved through copper catalysis under mild conditions of 50 °C with good to very good yields of up to 85 %. Furthermore, the dihydroquinolines' reactivity towards a denitrative alkylation of nitroolefins such as β‐nitrostyrene was discovered. Most importantly, the released biquinoline can be recycled, which greatly improves the overall atom‐economy of these alkyl radical precursors in comparison to previous N‐heterocyclic electroauxiliaries.
- Subjects
ALKYL radicals; SCISSION (Chemistry); COPPER; RADICALS (Chemistry); NITROALKENES; ALKYLATION
- Publication
Chemistry - A European Journal, 2023, Vol 29, Issue 50, p1
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.202301685