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 complete separation of the urea by-products. This paper describes the structure optimization study of the various TAP-supported carbodiimide reagents to obtain the desired reactivity and solubility profile. Furthermore, we have demonstrated that the diimide reagent can be regenerated from the urea to recycle the reagents.
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Ginisty et al. (2008) studied this question.
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