Study On C-H/C-S Bonds Activation Reactions And Their Application In The Synthesis Of Sulfonamides

Because of the wide range of biological activities of sulfonamides and their importance in the development of new drugs, expanding the repertoire of methods for the synthesis of these compounds is an important ongoing issue in organic and medicinal chemistry. The development of C-H bond and C-S bond activation offers more possibilities of efficient synthesis of them.We focus on the study of the methodology for the efficient synthesis of two kinds of sulfonamides via C-H bond and C-S bond activation. The main results of our research are as follows: Part Ⅰ:Copper-catalyzed intermolecular amidation of 8-methylquinolines via Csp3-H activationAlthough synthetic tools enabling Csp2-N bond formation have been well established, facile amination/amidation of Csp3-H bonds under mild conditions still remains a challenge in synthetic chemistry. The quinolin-8-ylmethanamine derivatives are valuable compounds, which have been reported as a building block in enormous areas involved in medicinal chemistry, organic synthesis, and analytical chemistry.8-Methylquinoline is an ideal substrate that could be used for the synthesis of quinolin-8-ylmethanamine derivatives via Csp3-H functionalization. An efficient copper-catalyzed C-H amidation of 8-methylquinolines with N-fluoroarylsulfonimides via Csp3-H activation is described. This reaction provides a novel approach to valuable quinolin-8-ylmethanamine derivatives in the absence of an additional oxidant.Part Ⅱ:Amidation of sulfides via C-S bond activationArylmethylsulfonamide derivatives are frequent structural motifs in biologically active molecules and pharmaceuticals. There is no report on the use of sulfides and sulfonamides as starting material for the synthesis of arylmethylsulfonamide derivatives via C-S bond activation. We have developed an efficient protocol to synthesis N-benzyl aryl sulfonamides via C-S bond activation. The reaction can proceed smoothly under metal free conditions for the synthesis of N- benzyl aryl sulfonamides. Therefore, this synthesis represents a useful extension of the existing synthetic routes to arylmethylsulfonamides.