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Metal Bridging for Directing and Accelerating Electron Transfer as Exemplified by Harnessing the Reactivity of AIBN
Author(s) -
Xie Yinjun,
Guo Shengmei,
Wu Longmin,
Xia Chungu,
Huang Hanmin
Publication year - 2015
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201411974
Subject(s) - chemistry , electron transfer , radical , redox , reactivity (psychology) , nucleophile , combinatorial chemistry , photochemistry , copper , catalysis , organic chemistry , medicine , alternative medicine , pathology
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.