Transition Metal Free N-arylation Of Amines By [Ar₃s][OTF]

Aromatic amines widely exists the stucture of nature product and pharmaceutical molecule.Transition metal catalyzed or-free N-arylation reaction is main strategy for the synthesis of arylamines.The study of trans-metal free N-arylation reaction are more less than trans-metal catalyzed N-arylation reaction,because of the majority of arylation reagent's activity is hard to implement direct N-arylation reaction of amines in the absence of transition metal.So it is significance for the development of new arylation reagent that could achieve the transition metal free N-arylation reaction of amines.For the past few years,the many research of arylsulfonium salts as aryltion reagent were reported in which participated to build of organic and pharmaceutical molecule,but these paper mostly focus on transition metal catalyzed coupling reaction compared with the transition metal free arylation,even the transition metal free N-arylation of amines while use triarylsulfonium salts as arylation reageats has never been known.In this thesis,we developed a transition metal free N-arylation reaction of amines through triarylsulfonium salts as arylation reagent and t-BuOK or KOH as base.Furthermore,we could selectively synthsized mono-or di-N-arylation compound by changed the scale of triarylsulfonium salts and base,in the moderate to excellent yields.The reaction plausible mechanism are confirmed that base-mediated formation of aryne intermediate from contained-substituent group triarylsulfonium salts,then the addition of aryne and amines to give the N-arylation product.Overall,we firstly developed triarylsulfonium salts as arylation reagent to achieved transition metal free N-arylation reaction,and demonstrating triarylsulfonium salts is one kind of powerful aryne precursor.This method would be refer to the further application of arylation reaction by triarylsulfonium salts.