Journal of Organic Chemistry
Journal of Organic Chemistry
5 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

You might also like
Discover & Discuss Important Research

Keeping up-to-date with research can feel impossible, with papers being published faster than you'll ever be able to read them. That's where Researcher comes in: we're simplifying discovery and making important discussions happen. With over 19,000 sources, including peer-reviewed journals, preprints, blogs, universities, podcasts and Live events across 10 research areas, you'll never miss what's important to you. It's like social media, but better. Oh, and we should mention - it's free.

  • Download from Google Play
  • Download from App Store
  • Download from AppInChina

Researcher displays publicly available abstracts and doesn’t host any full article content. If the content is open access, we will direct clicks from the abstracts to the publisher website and display the PDF copy on our platform. Clicks to view the full text will be directed to the publisher website, where only users with subscriptions or access through their institution are able to view the full article.