Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 54, Issue 20, Pages 5900-5904Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201411974
Keywords
AIBN; cinnamic acids; copper; enolates; single-electron transfer
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Funding
- Chinese Academy of Sciences
- National Natural Science Foundation of China [21222203, 21372231, 21133011]
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A new strategy for tuning the electron transfer between radicals and enolates has been developed. This method elicits the innate reactivity of AIBN with a copper catalyst and enables a cascade reaction with cinnamic acids. Electron paramagnetic resonance studies and control experiments indicate that the redox-active copper species not only activates the radical by coordination, but also serves as a bridge to bring the radical and nucleophile within close proximity to facilitate electron transfer. By exploiting possible combinations of redox-active metals and radical entities with suitable coordinating functional groups, this strategy should contribute to the development of a broad range of radical-based reactions.
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