Study On The [Cp^*IrCl₂]₂-catalyzed C-H Bond Activation/annulation To Construct Heterocyclic Compounds

The synthesis of high value-added chemicals through cheap and readily available starting materials is of great research value in synthetic chemistry.Among which,the transition metals such as iridium,rhodium,ruthenium,palladium,cobalt and others catalyzed cascade C-H bond activation/annulation for the construction of C-C bonds or C-hetero bonds,and does not need to prefunctionalize the substrate.It has the characteristics of green and atomic economy,and has a wide range of application in the synthesis of pharmaceuticals,natural products and others.The introduction of directing groups enables highly selective C-H bond functionalization reactions,among which oxygen-and nitrogen-containing directing groups are the most common.In this thesis,we mainly describe the[Cp^*IrCl₂]₂catalyzed direct C-H bond activation/annulation reaction toward diverse heterocycles and 1,4-dicarbonyl compounds.The main content includes two parts as follows:（1）[Cp^*IrCl₂]₂-catalyzed synthesis of 7H-indolo[2,3-c]quinoline from indole and nitroneIn this work,we have developed an expedient synthesis of the useful7H-indolo[2,3-c]quinolines by a novel iridium-catalyzed C-2 and C-3 dual C-H bond functionalization of indoles with nitrones.This protocol features mild conditions,broad scope,and good functional group compatibility.Meanwhile,the reaction can be scaled up to the gram scale.UV-vis and fluorescence spectral analyses of these highly fused heteroarenes were performed.（2）[Cp^*IrCl₂]₂-catalyzed regio-selective C（sp³）-H bond insertion reaction of2-acylimidazoles with sulfoxide ylide.In this work,we have developed an iridium-catalyzed C（sp³）-H bond insertion reaction of 2-acylimidazoles with sulfoxide ylides to access a series of 1,4-dicarbonyl compounds by using sulfoxonium ylides as an efficient and stable carbene precursor.The main procedure involved C（sp³）-H bond activation,carben migratory insertion,and protonation.This protacol features with mild reaction conditions,wide substrate scope,and excellent regioselectivity.