Versatile, easy methodology for oxidative functionalization of aldehydes using acetamido-TEMPO and sodium persulfate

LEÓN SANDOVAL, ARTURO; POLITANO, FABRIZIO; WITKO, MASON L.; LEADBEATER, NICHOLAS E.

Atlanta, GA.

Conferencia; ACS Fall 2021; 2021

American Chemical Society

A simple and robust, metal-free route for the oxidative functionalization of aldehydes to yield hexafluoroisopropyl (HFIP) esters and N-acyl azoles is described. The methodology employs sodium persulfate as a primary oxidant and a catalytic quantity of 4-acetamido-2,2,6,6-tetramethylpiperidine-1-oxyl (ACT). It is applicable to aromatic, heteroaromatic, and aliphatic aldehydes. This new protocol offers a more accessible and cheaper alternative to oxidative esterification and amidation of aldehydes, and open avenues for the exploration of others oxidative functionalization reactions.