Solvent-Directed Transition Metal-Free C-C Bond Cleavage by Azido-1,3,5-triazines and Their Stability-Reactivity Paradox

We report a solvent-directed and regioselective carbon-carbon bond cleavage of aryl ketones by azido-1,3,5-triazines (ATs), which is typically completed within 10 min in DMSO at room temperature, without using transition metal catalysts. The cleavage is driven by the steric hindrance in the adducts of aryl ketones and ATs, which is substantiated by DFT calculation. Our recent results showed that ATs present high reactivity in solution and high stability in solid state. This stability-reactivity paradox has been explained in light of the molecular and crystal structures of ATs.

Automated summary

The study presents a solvent-directed and regioselective carbon-carbon bond cleavage method using azido-1,3,5-triazines (ATs) that does not require transition metal catalysts. The cleavage is driven by steric hindrance in the adducts of aryl ketones and ATs, while the high reactivity and stability of ATs in solution and solid state are explained by their molecular and crystal structures.