Transformation Of B-B Bond In B(3,6)-dipinacolatoboryl-o-carborane

Carboranes have a wide range of applications in medicinal chemistry,coordination chemistry and material science.The development of new type preparation methods for carborane derivatives has become one of the core issues in carborane chemistry.This thesis firstly reviewed well-developed methods for BH vertex functionalization of o-carborane,including non-transition-metal catalyzed and transition-metal catalyzed reactions.Then,the reactivity of B-B bond in organoboron reagent was briefly introduced.The study showed that borylated carborane can be important intermediate applied to further transformations.This thesis mainly includes the following two aspects:1.Transformation of Bpin?pinacolatoboryl?of B?3,6?-diborylated-o-carborane to different functional groups including cyano,fluoride,carbonylation,cyanide or arylation,and the addition of B-B bond to olefine/alkyne.2.Optimize the arylation reaction conditions of B?3,6?-diborylated-o-carboranes and explore aromatic substrate scope.This thesis studied a series of transformation reaction based on the important intermediate of B?3,6?-diborylated-o-carborane,and developed the arylation system of PdCl₂?cod?and tricyclohexylphosphine in Suzuki Coupling reaction.A series of new arylation products of B?3,6?-diarylated-o-carborane was obtained inmoderate yields.The formation of new compounds was demonstrated by Nuclearmagnetic resonance,Gas chromatography-mass spectrometry,Elemental analysis or High resolution mass spectrometry.In addition,this reaction also enriched the synthetic methodology for carborane functionalization.