Access to Biaryls via Anilide C-N Bond Activation through Photocatalytic Radical Truce-Smiles Rearrangement
Sharmila Das1, Samrat Kundu1, Rik Banerjee1
1Department of Chemistry, Indian Institute of Technology Kharagpur, Kharagpur 721302, India.
None:
C(aryl)-N bond activation of widely available anilines under mild conditions remains underdeveloped owing to the inert nature of anilines. Herein, Truce-Smiles rearrangement is employed to address this challenge by using naphthocarbazole as an organo-photoreductant, via a single-electron transfer process from readily accessible aryl chlorides and bromides tethered to anilines. This method offers a wide range of synthetically challenging 2-amidobiaryls, including sterically demanding ones. DFT calculations and control experiments were performed to elucidate the underlying reaction pathway.
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