Studies On The Palladium-catalyzed Reactions Of Aliphatic Nitriles With Organoborane Reagents

Recent advances in the transition metal-catalyzed addition of nitrile to arylation reagents were reviewed.The thesis will be focused on this subject to carry out transition metal-catalyzed addition of organoboron reagents to aliphatic nitriles.This thesis is divided into six chapters:In the first chapter,recent advances in the transition metal-catalyzed addition of nitriles with arylation reagents were reviewed.In the second chapter,palladium-catalyzed addition of potassium aryltrifluoroborates to succinonitrile(or 4-oxo-4-phenylbutanenitrile)has been developed,leading to symmetric(or asymmetric)1,4-diketones.This synthetic method features mild reaction conditions,broad scope and high functional group tolerance.In the third chapter,we developed a palladium-catalyzed addition of potassium aryltrifluoroborates to succinonitrile(or 4-oxo-4-phenylbutanenitrile),leading to symmetric(or asymmetric)2,5-diarylpyrroles in one-pot.This synthetic method provides a new pathway to to structurally diverse 2,5-diarylpyrroles.In the fourth chapter,we developed a palladium-catalyzed addition of potassium aryltrifluoroborates to glutaronitrile for the synthesis of 2,6-diarylpyridines,providing an efficient synthetic strategy for the synthesis of pyridines.In the fifth chapter,we developed a palladium-catalyzed tandem addition/cyclization of arylboronic acids with methyl 2-(cyanomethyl)benzoate,affording isoquinolinones in moderate to excellent yields.This synthetic method features mild reaction conditions,broad scope and high functional group tolerance.The utility of this methodology was further applied to the total synthesis of CWJ-a-5,which was the representative compound identified as a topoisomerase 1 inhibitor.Preliminary mechanistic experiments are investigated.In the sixth chapter,experimental section including the experimental procedures and characterization data are described.