Studies On Palladium-catalyzed Reactions Between Arylboronic Acids With Anhydride Derivatives

Compared with other organometallic reagents, organoborane reagenthas been winning high prestige in palladium-catalyzed organic reactionsin recent years due to its obvious advantages, such as low toxicity,resistance to air or water, good functional compatibility, facile synthesisand commercial available etc. This thesis will be focused onpalladium-catalyzed esterification reactions and Suzuki-Type couplingreactions of arylboronic acids with anhydride derivatives.First, recent advances in the transition metal-catalyzed esterificationreactions and Suzuki-Type coupling reactions were reviewed, thendifferent systems of palladium-catalyzed reactions between arylboronicacids with anhydride derivatives were studied:(1) A mild and effectivesynthesis of aryl benzoate compounds by PdCl2(PPh3)2-catalyzedesterification reaction between arylboronic acids with benzoic anhydridesis described.(2) Pd2(dba)3/DPEphos-catalyzed esterification of arylboronic acids with isatoic anhydrides for the synthesis of arylo-aminobenzoate derivatives is systematic investigated. Preliminarymechanistic experiments using deuterium labeling showed that theoxygen atom was derived from dioxygen.(3) Pd(OAc)2-catalyzedSuzuki-Type coupling reaction of arylboronic acids with isatoicanhydrides, leading to diaryl o-aminoketones.