3 years ago

Radical Addition/Insertion/Cyclization Cascade Reaction To Assemble Phenanthridines from N-Arylacrylamide Using Cyano as a Bridge under Photoredox Catalysis

Radical Addition/Insertion/Cyclization Cascade Reaction To Assemble Phenanthridines from N-Arylacrylamide Using Cyano as a Bridge under Photoredox Catalysis
Weiwen Yuan, Yulan Yu, Peipei Sun, Ping Liu, Zhiqiang Cai
A radical addition/nitrile insertion/homolytic aromatic substitution (HAS) cascade reaction to prepare 6-quaternary alkylated phenanthridines was developed. The addition of the active methylene radicals which were generated from 2-bromoacetonitrile, ethyl 2-bromoacetate, 2-bromo-N,N-dimethylacetamide, or 2-bromo-1-phenylethan-1-one to carbon–carbon double bonds of N-arylacrylamides followed by the cyano-participating sequential cyclization produced a series of phenanthridines in moderate to good yields under photoredox catalysis.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b01447

DOI: 10.1021/acs.joc.7b01447

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