α-Acetoxyarone synthesis via iodine-catalyzed and tert-butyl hydroperoxide-mediateded self-intermolecular oxidative coupling of aryl ketones.

ABSTRACT: We present a metal-free method for α-acetoxyarone synthesis by self-intermolecular oxidative coupling of aryl ketones using I₂-tert-butyl hydroperoxide (TBHP). Under the optimum conditions, various aryl ketones gave the corresponding products in moderate to excellent yields. A series of control experiments were performed; the results suggest the involvement of radical pathways. Multiple radical intermediates were generated in situ and the overall process involved several different reactions, which proceeded self-sequentially in a single reactor. A labeling experiment using ¹⁸O-labeled H₂O confirmed that the oxygen in the product was derived from TBHP, not from H₂O in the TBHP solvent.

SUBMITTER: Tan L 

PROVIDER: S-EPMC5480364 | biostudies-literature | 2017

REPOSITORIES: biostudies-literature