Site- and stereoselective silver-catalyzed intramolecular amination of electron-deficient heterobenzylic C-H bonds.

ABSTRACT: We report a method for the site- and stereoselective intramolecular amination of electron-deficient heterobenzylic C-H bonds via silver-catalyzed nitrene transfer (NT). A silver complex supported by a tripodal piperidine-based ligand afforded excellent reactivity under mild conditions (up to 96% yield), site-selectivity (up to >20 : 1), and diastereoselectivity (up to >20 : 1 dr) for the amination of heterobenzylic C-H bonds that reacted poorly with other metal-based catalysts for NT. Our catalyst proved highly amenable to substrates bearing diverse competing sites for functionalization, including complex molecules derived from pharmaceuticals and natural products. Ligand screening revealed the importance of scaffold rigidity, leading to the discovery of an analogous quinuclidine-ba

SUBMITTER: Trinh TA 

PROVIDER: S-EPMC11815850 | biostudies-literature | 2025 Mar

REPOSITORIES: biostudies-literature