N-METHYL-4-PICOLINIUM IODIDE ESTERS AS VISIBLE LIGHT PHOTOREMOVABLE PROTECTING GROUPS FOR CARBOXYLIC ACIDS

Abstract

Facile photorelease of carboxylic acids is performed through charge-transfer excitation of N-methyl-4-picolinium iodide esters. Photolysis reactions are carried out under mild, biphasic solvent conditions using a household LED lamp. Release is quantified by 1H NMR analysis and carboxylic acid release is reported in high yields. The viability of this method for synthetic chemistry is demonstrated through a macroscale photolysis. Additionally, the potential for solvent-independent NAP ester charge-transfer photolysis is explored.