1,1′-Diarylethylene\nas a Key Additive for the\nVisible Light Synthesis of Bioactive Dihydrobenzo[<i>a</i>]phenanthridine Compounds
This\nstudy introduces a straightforward synthetic approach for\ngenerating 7,8-dihydrobenzo[<i>a</i>]phenanthridine analogs\nthrough visible-light-induced cyclization, showing promise as antitumor\nagents. Unexpectedly, the incorporation of 1,1′-diarylethylene\nas an additive significantly boosts yield. Through mechanistic investigations,\nwe uncover its crucial role as a trap for the methyl radical formed\nafter the N–O bond cleavage of <i>O-</i>acetyl oxime,\npromoting intramolecular cyclization of a nitrogen-centered imine\nradical. These insights into the mechanism pave the way for transformative\nadvancements in this synthesis strategy.
Publication Details
- Journal
- Figshare
- Published
- 2024-10-01
- DOI
- https://doi.org/10.1021/acs.joc.4c01891.s001
- Primary Topic
- Radical Photochemical Reactions
- Type
- article
- Field-Weighted Citation Impact
- 0.00