As important intermediates in organic reacton, arynes have attracted a great deal of attention owing to their highly reactive property. Since the milder preparation of benzynes was developed, it has made considerable progress on numerous reactions and applications in organic synthesis. Arynes are widely used in organic transformation to construct 1,2-disubstituted arenes and other useful compounds containing aryl groups. The thesis explores the addition-cyclization cascade reaction of salicyl N-tosylimines with arynes, which are formed from silylaryl triflates in the presence of fluorion. The cas-cade reaction provides a mild and efficient method for facile synthesis of N-(9-xanthyl)-4-toluenesulfonamides. In addition, the cascade promote the formation of C－O and C－C bonds in one step, and the mild conditions are compatible with a variety of functional groups in this high yield reaction. We have developed a mild and efficient entry point into the synthesis of 9-amine xanthenes. Based on the aforementioned studies, the reaction of benzynes with the chiral imine (N-tert-butyl sulfonamide with 4-bromo-salicyladehyde in a condensation reaction) was explored. We hope to get a good stereoselectivity in this reaction by using the chiral group. As a result, the experiments show that the overall yield is 89% in CsF-CH3CN system, however, the diastereoselectivity of product is poor (d.r. = 1.4:1). Key Words: N-(9-xanthyl)-4-toluenesulfonamides, salicyl N-tosylimines, arynes, addition-cyclization, cascade.