Construction of Oxo-Bridged Diazocines via Rhodium-Catalyzed (4+3) Cycloaddition of Carbonyl Ylides with Azoalkenes

Developing efficient strategies for synthesizing novel diazocine compounds is valuable because their use has been limited by their synthetic accessibility. This work describes the catalytic (4+3) cycloaddition reaction of carbonyl ylides with azoalkenes generated in situ. The rhodium-catalyzed cascade reaction features good atom and step economy, providing the first access to oxo-bridged diazocines. The product could be synthesized on a gram scale and converted into diversely substituted dihydroisobenzofurans.

Automated summary

Developing efficient strategies for synthesizing novel diazocine compounds is valuable due to limited synthetic accessibility. This work describes the catalytic reaction between carbonyl ylides and in situ generated azoalkenes, resulting in the synthesis of oxo-bridged diazocines. The product could be obtained on a gram scale and converted into diversely substituted dihydroisobenzofurans.