Pd-catalyzed sequential distal C-H alkenylation and π-allylic amination of arylacetic acids using MBH acetates: access to macrocyclic lactams.

ABSTRACT: Palladium(ii)-catalyzed directed meta-selective C-H functionalization of arylacetic acids has been accomplished utilizing Morita-Baylis-Hillman (MBH) acetates as the coupling partner to furnish β-aryl MBH acetates that can be converted into 14-membered macrocyclic lactams employing water as the oxygen source via a π-allyl intermediate. The sequential meta/meta' C-H difunctionalization can be accomplished with varied coupling partners. Mechanistic investigations underscore the roles of the nitrile-directing template, palladium(ii)-catalysis and ligand in meta-selectivity. The macrocyclization pathway has been validated through an ¹⁸O-labeling experiment and the photophysical studies reveal distinct fluorescence in the selected macrocycles. In ad

SUBMITTER: Muthuraja P 

PROVIDER: S-EPMC12616709 | biostudies-literature | 2026 Jan

REPOSITORIES: biostudies-literature