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Transition‐Metal‐Free Synthesis of Phenanthridinones through Visible‐Light‐Driven Oxidative C–H Amidation
Author(s) -
Usami Kaoru,
Yamaguchi Eiji,
Tada Norihiro,
Itoh Akichika
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201900536
Subject(s) - chemistry , visible spectrum , transition metal , photochemistry , amide , electron transfer , catalysis , proton coupled electron transfer , aryl , oxidative phosphorylation , proton , organic chemistry , quantum mechanics , biochemistry , physics , alkyl , optoelectronics
The treatment of N ‐aryl biphenylcarboxamide, 1‐chloroanthraquinone (1‐Cl‐AQN) catalyst, and K 2 CO 3 in CHCl 3 under visible light irradiation affords phenanthridinone via radical cyclization. This reaction proceeds under transition‐metal‐free condition, room temperature, and direct C–H amidation. Mechanistic studies indicate that amidyl radical generation proceeds by visible light induced proton coupled electron transfer (PCET) from N–H bond of the amide.