In this study, we investigate the mechanochemical activation of acyl azide for direct C-H amidation with excellent C-N bond selectivity, fast rate, enhanced reactivity, solvent-free condition, and broad scope. Thermally unstable acyl azide, prone to Curtius rearrangement, was found to be controllable under mechanochemical ball milling conditions. Investigation of the mechanochemical process window of acyl azide led us to define highly selective Cp*Ir(III)-catalyzed acyl azide activation to acyl nitrene species and direct C-H amidation protocol. In addition to the expected merits of mechanochemistry, the newly developed high-speed ball milling method allows for carbamoyl azide utilization, which showed a limited scope under thermal solution conditions, registering to a list of mechanochemically preferred reactions.
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© 2021 American Chemical Society
All Science Journal Classification (ASJC) codes
- General Chemistry
- Environmental Chemistry
- General Chemical Engineering
- Renewable Energy, Sustainability and the Environment