Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 58, Issue 2, Pages 526-531Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201810261
Keywords
amination; late-stage functionalization; photoredox catalysis; pyridyl radical cation; radical mechanism
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Funding
- ETH Zurich
- NSERC
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Electron-transfer photocatalysis provides access to the elusive and unprecedented N-pyridyl radical cation from selected N-substituted pyridinium reagents. The resulting C(sp(2))-H functionalization of (hetero)arenes furnishes versatile intermediates for the development of valuable aminated aryl scaffolds. Mechanistic studies that include the first spectroscopic evidence of a spin-trapped N-pyridyl radical adduct implicate SET-triggered, pseudo-mesolytic cleavage of the N-X pyridinium reagents mediated by visible light.
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