Instituto de Ciencias Químicas, Facultad de Ciencias, Isla Teja, Universidad Austral de Chile, 5090000, Valdivia, Chile.
Universidad de Castilla-La Mancha, Departamento de Química Inorgánica, Orgánica y Bioquímica-Centro de Innovación en Química Avanzada (ORFEO-CINQA), Facultad de Ciencias y Tecnologías Químicas, Avda. Camilo José Cela, 10, 13071, Ciudad Real, Spain.
Chempluschem. 2021 Mar;86(3):460-468. doi: 10.1002/cplu.202100079.
Bio-derived furan- and diacid-derived cyclic carbonates have been synthesized in high yields from terminal epoxides and CO . Furthermore, four highly substituted terpene-derived cyclic carbonates were isolated in good yields with excellent diastereoselectivity in some cases. Eleven new cyclic carbonates derived from 10-undecenoic acid under mild reaction conditions were prepared, providing the corresponding carbonate products in excellent yields. The catalyst system also performed the conversion of an epoxidized fatty acid n-pentyl ester into a cyclic carbonate under relatively mild reaction conditions (80 °C, 20 bar, 24 h). This bis(cyclic carbonate) was obtained in high yields and with different cis/trans ratios depending on the co-catalyst used. An allyl alcohol by-product was only observed as a minor product when bis(triphenylphosphine)iminium chloride was used as co-catalyst. Finally, two cyclic carbonates were used as building blocks for the preparation of non-isocyanate poly(hydroxy)urethanes by reaction with 1,4-diaminobutane.
生物衍生呋喃和二酸衍生环状碳酸酯已通过末端环氧化物和 CO 高产率合成。此外，在某些情况下，以高非对映选择性从四个高度取代的萜烯衍生环状碳酸酯中分离出四个高取代的萜烯衍生环状碳酸酯。在温和的反应条件下，从 10-十一烯酸制备了 11 种新的环状碳酸酯，以优异的产率提供了相应的碳酸酯产物。该催化剂体系还在相对温和的反应条件（80°C，20 bar，24 h）下将环氧化脂肪酸正戊酯转化为环状碳酸酯。该双（环状碳酸酯）以高产率获得，并且根据所用共催化剂的不同，具有不同的顺/反式比例。当使用双（三苯基膦）亚胺氯化物作为共催化剂时，仅观察到作为次要产物的烯丙醇副产物。最后，两种环状碳酸酯被用作与 1,4-丁二胺反应制备非异氰酸酯聚（羟基）脲的构建块。
