Chan-Lam Reaction and Lewis Acid Promoted 1,3-Rearrangement of N-O Bonds to Prepare N-(2-Hydroxyaryl)pyridin-2-ones

We describe the difunctionalization of arylboronic acids to prepare various N-(2-hydroxyaryl)pyridin-2-ones in good yields using N-hydroxypyridin-2-ones as the oxygen and nitrogen sources through a copper(II)-catalyzed Chan-Lam reaction and subsequent BF3 promoted selective 1,3-rearrangement of N-O bond in a one-pot procedure. Mechanistic studies reveal that the 1,3-rearrangement selectivity is controlled by the formation of the key aryloxypyridinium salt. The obtained products are easily converted to various useful pyridin-2-one scaffolds.

Automated summary

By employing N-hydroxypyridin-2-ones as the oxygen and nitrogen sources, arylboronic acids were difunctionalized successfully to prepare various N-(2-hydroxyaryl)pyridin-2-ones in good yields through a copper(II)-catalyzed Chan-Lam reaction and subsequent BF3 promoted selective 1,3-rearrangement. Mechanistic studies revealed that the selectivity of the 1,3-rearrangement is controlled by the formation of the key aryloxypyridinium salt. The obtained products can be easily converted to various useful pyridin-2-one scaffolds.