Studies On The Aryl C-H Bond Halogenation And Sulfonylation With Copper Catalysis Or Promotion

Transition metal such as copper-catalyzed aromatic C-H activation and functionalization constitute the central content of current organic synthesis.These transformations play irreplaceable role in the synthesis of functional organic compounds,pharmaceuticals and natural products.This thesis reports copper-catalyzed or promoted C-H activation and functionalization reactions via halogenation and sulfonylation,and consists of three main sections.(1)Copper-catalyzed one-pot tandem synthesis of 5-halogenated 8-aminoquinolines.Using acyl halide and 8-aminoquinoline as starting materials,the tandem N-acylation and C5-H halogenation are furnished in one step in the presence of copper catalyst.In this method,acy halide acts as both the donors of acyl and halogen source,no additional halogen donor is required.(2)Copper-catalyzed indole sective C3-sulfonylation.By employing indole and sodium arenesulfinates as substrates and Cu I as catalyst,the selective C3-sulfonylation of indole is accomplished.This method features mild reaction conditions,short reaction time as well as the satisfactory yield in gram scale synthesis.(3)Copper-promoted tandem N-acylation and C-H sulfonylation for the synthesis of 5-sulfonyl-8-aminoquinolines.Directly subjecting 8-aminoquinoline,acyl chloride and sodium phenylsulfinite for three-component reaction,the tandem N-acylation and directed C5-sulfonylation are realized via the promotion of Cu(II)salt,providing step economical new method for the synthesis of 5-sulfonyl-8-aminoquinolines.