Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 57, Issue 47, Pages 15517-15522Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201809879
Keywords
C-H activation; heterocycles; photochemistry; radicals; reaction mechanisms
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Funding
- Institute for Basic Science [IBS-R010-G1, IBS-R010-D1]
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Metal-free, visible-light-induced site-selective heter-oarylation of remote C(sp(3))-H bonds has been accomplished through the design of N-alkoxyheteroarenium salts serving as both alkoxy radical precursors and heteroaryl sources. The transient alkoxy radical can be generated by the single-electron reduction of an N-alkoxypyridinium substrate by a photo-excited quinolinone catalyst. Subsequent radical translocation of the alkoxy radical forms a nucleophilic alkyl radical intermediate, which undergoes addition to the substrate to achieve remote C(sp(3))-H heteroarylation. This cascade strategy provides a powerful platform for remote C(sp(3))-H heteroarylation in a controllable and selective manner and is well suited for late-stage functionalization of complex bioactive molecules.
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