Tetraarylphosphonium-supported carbodiimide reagents: synthesis, structure optimization and applications.
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.
Ginisty
Maryon
M
Département de Chimie, Université de Montréal, PO Box 6128, Station Downtown, Montréal, Canada QC H3C 3J7.
Roy
Marie-Noelle
MN
Poupon
Jean-Christophe
JC
Picard
Anne
A
Charette
André B
AB
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
D000577:Amides; D002234:Carbodiimides; D004952:Esters; D009943:Organophosphorus Compounds; D014867:Water