Copper-Catalyzed Three-Component Carboboronation of Allenes Using Highly Strained Cyclic Ketimines as Electrophiles
Hao Deng, Yujie Dong, Yu Shangguan, Fazhou Yang, Sheng Han, Jiaqi Wu, Bo Liang, Hongchao Guo, Cheng Zhang
Abstract
A diastereoselective copper and NHC-ligand-catalyzed three-component difunctionalization of allenes with bis(pinacolato)diboron and 2H-azirines to afford borylated allylaziridines is described. The reaction exhibits complete diastereoselectivity and good yields, and the further chlorination of the corresponding borylated products was also performed. It is believed that the high ring-strain force of 2H-azirines facilitates the reaction. More chemical transformations of borylated allylaziridines are also reported.
Topics & Concepts
ChemistryElectrophileCatalysisLigand (biochemistry)Ring (chemistry)CopperComponent (thermodynamics)Ring strainCombinatorial chemistryMedicinal chemistryOrganic chemistryReceptorPhysicsThermodynamicsBiochemistryOrganoboron and organosilicon chemistryCatalytic C–H Functionalization MethodsCarbon dioxide utilization in catalysis