Photocatalytic 1,2-oxo-alkylation reaction of styrenes with diazoacetates

We report on the photocatalytic 1,2-difunctionalization reaction of styrenes with acceptor-only diazoalkanes. In the presence of DABCO and tBuOOH, the carbene reactivity of diazoalkanes can be suppressed and a 1,2 oxo-alkylation reaction can be achieved (32 examples, up to 94% yield) without the formation of cyclopropane by-products via the formation of radical intermediates from ethyl diazoacetate.

Automated summary

This study reports on the photocatalytic 1,2-difunctionalization reaction of styrenes with acceptor-only diazoalkanes. By using DABCO and tBuOOH, the carbene reactivity of diazoalkanes can be suppressed, allowing for a 1,2 oxo-alkylation reaction to occur with high yield (up to 94%), without the formation of cyclopropane by-products via radical intermediates from ethyl diazoacetate.