Solvent-controlled, chemodivergent oxidative anionic Fries rearrangement of O-aryl carbamates under aerobic conditions.

ABSTRACT: We disclose herein a mild and efficient organolithium-mediated protocol which enables the chemodivergent transformation of ortho-cresol-derived O-aryl carbamates into diverse molecular structures by simply changing the nature of the reaction medium, working under air and at room temperature. The use of the biobased 2-MeTHF as solvent allows the chemoselective preparation of α-hydroxy arylacetamides in a single synthetic operation with a remarkable functional group tolerance. Our strategy, which exploits the presence of molecular oxygen arising from the use of bench-type aerobic conditions, relies on a one-pot anionic homo-Fries rearrangement/amide enolate autoxidation sequence with two consecutive C-C/C-O bond formation events occurring at the same carbon atom. Further

SUBMITTER: Gnavi R 

PROVIDER: S-EPMC12841593 | biostudies-literature | 2026 Jan

REPOSITORIES: biostudies-literature