Improved synthesis of phosphonium-supported carbodiimide reagents and applications

ORGN 162

Andre B. Charette, andre.charette@umontreal.ca, Maryon Ginisty, antara78@yahoo.fr, and Marie-Noelle Roy, mn.roy@umontreal.ca. Department of Chemistry, Université de Montréal, C.P. 6128, succ. Centre-ville, Montreal, QC H3C 3J7, Canada
New tetraarylphosphonium (TAP)-supported alkyl- and arylcarbodiimides were synthesized and used as coupling reagents for esterification reactions, amidation reactions and dehydration reactions of hydroxyesters. Taking advantage of the solubility properties imparted by the tetraarylphosphonium unit, a simple precipitation and filtration allowed the separation of the by-products resulting from the carbodiimide reagent. This poster describes the structure optimization study of the various TAP-supported carbodiimide reagents to obtain the desired reactivity and solubility profile. Once determined, the synthesis was shorten significantly from 6 to 3 steps.