Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 54, Issue 13, Pages 4055-4059Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201411342
Keywords
acyl oximes; N heteroarenes; iminyl radicals; photochemistry; visible light
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Funding
- National Basic Research Program of China [2011CB935800]
- 863 Program [2013AA092903]
- National Natural Science Foundation of China [21121091, 21272113, 21372115]
- Natural Science Foundation of Jiangsu Province [BK2012012, BK20131266]
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A unified strategy involving visible-light-induced iminyl-radical formation has been established for the construction of pyridines, quinolines, and phenanthridines from acyl oximes. With fac[Ir(ppy)(3)] as a photoredox catalyst, the acyl oximes were converted by 1e(-) reduction into iminyl radical intermediates, which then underwent intramolecular homolytic aromatic substitution (HAS) to give the N-containing arenes. These reactions proceeded with a broad range of substrates at room temperature in high yield. This strategy of visible-lightinduced iminyl-radical formation was successfully applied to a five-step concise synthesis of benzo[c]-phenanthridine alkaloids.
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