Abstract
A facile preparation of 3-hydroxylisoquinolin-1, 4-diones and piperidine-2,5-dione from alkyne-tethered amide is reported under cerium photocatalysis and O2 balloon. The reaction works well with a broad reaction scope and reaction efficiency. Mechanism studies indicate that 3-hydroxylpyrrolidin-2-one-containing α-ketol radical species serves as a possible key intermediate, and the final product is attributed to a formal N-centered radical initiated [2 + 2] cyclization and α-ketol rearrangement. Interestingly, divergence towards CN bond migration and CC bond migration is reached in this radical α-ketol rearrangement.
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