title: Tetraarylphosphonium-supported carbodiimide reagents: synthesis, structure optimization and applications.
abstract: 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.
authors.affiliation: Département de Chimie, Université de Montréal, PO Box 6128, Station Downtown, Montréal, Canada QC H3C 3J7.
authors.forename: Maryon
authors.initials: M
authors.lastname: Ginisty
authors.forename: Marie-Noelle
authors.initials: MN
authors.lastname: Roy
authors.forename: Jean-Christophe
authors.initials: JC
authors.lastname: Poupon
authors.forename: Anne
authors.initials: A
authors.lastname: Picard
authors.forename: André B
authors.initials: AB
authors.lastname: Charette
mesh_terms: D000577:Amides / Q000138:chemical synthesis* / Q000737:chemistry*; D002234:Carbodiimides / Q000737:chemistry*; D004951:Esterification; D004952:Esters / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D009943:Organophosphorus Compounds / Q000737:chemistry*; D013237:Stereoisomerism; D014867:Water / Q000737:chemistry
chemical_list: D000577:Amides; D002234:Carbodiimides; D004952:Esters; D009943:Organophosphorus Compounds; D014867:Water