Ginisty Maryon, Roy Marie-Noelle, Poupon Jean-Christophe, Picard Anne, Charette André B
Département de Chimie, Université de Montréal, PO Box 6128, Station Downtown, Montréal, Canada QC H3C 3J7.
J Org Chem. 2008 Apr 4;73(7):2542-7. doi: 10.1021/jo702417v. Epub 2008 Mar 4.
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.
合成了新型四芳基鏻（TAP）负载的烷基和芳基碳二亚胺，并将其用作羟基酯酯化反应、酰胺化反应和脱水反应的偶联试剂。利用四芳基鏻单元赋予的溶解性，通过简单的沉淀和过滤即可完全分离脲副产物。本文描述了各种TAP负载的碳二亚胺试剂的结构优化研究，以获得所需的反应活性和溶解性。此外，我们还证明了二亚胺试剂可从脲中再生以实现试剂的循环利用。
