Copper-catalyzed Chan Lam Coupling Reaction To Construct Triaryl-containing Sulfenamide Scaffolds

As an important class of organic structures,sulfenamide derivatives widely exist in natural products and drug molecules.Sulfenamides were widely applied in the fields of rubber industry,pesticide chemistry,new drug research and development,organic synthesis and peptide synthesis due to their specific S-N bond.Additionally,the sulfur atom in hyposulfonamide has a low valence state,which could finally be used as a significant synthetic intermediate for the formation of sulfonimide,sulfonamide,sulfoxide amide and other related compounds.Recently,The methods for the construction of subsulfenamide skeletons have received widespread attention.However,to our knowledge,the reported routes are all for the formation of alkyl subsulfenamides.The strategy for the construction of subsulfenamide scaffolds with triaryl group is still limited.Therefore,we try to develop an efficient method for the synthesis of sulfenamides with triaryl group.In this paper,the synthetic method for sulfenamides with triaryl group has described.Firstly,we optimized the reaction conditions.The optimal reaction conditions as follows:S-(4-fluorophenyl)-N-phenylthiohydroxylamine(1.0 equiv,0.15 mmol),p-methylphenylboric acid(2.0 equiv),copper trifluoroacetate hydrate(10mol%),ligand L20(20 mol%),azomethyldicyclohexylamine(1.5 equiv),acetonitrile as solvent(0.5 m L)and stirred at room temperature for 24 hours under oxygen conditions.With the optimized reaction conditions in hand,we investigated the scope of this coupling reaction.This method provides a series of sulfenamide compounds with triaryl group in moderate to excellent yields with good functional tolerance.