Study On The Synthesis,of Primary Aryl Sulfonamides And Amides Via Copper-Mediated C-N Bond Cleavage

This thesis mainly focused on the study of the copper-catalyzed C-N bonds cleavage for the synthesis of primary aryl sulfonamide and primary aryl amides.The sulfonamide and amides are two kinds of important pharmaceutical intermediates.The present protocol further enriches the organic methodology for the synthesis of sulfonamide and amides derivatives.This thesis mainly includes two parts:?a?Copper-catalyzed C-N bond cleavage for the synthesis of primary aryl sulfonamidesAn efficient protocol for the synthesis of primary aryl sulfonamides from easily available N-arylsulfonyl amino acids via copper-catalyzed C-N bond cleavage has been developed in the presence of 0.3 equiv of CuO,in DMSO at 100?for 8 hours.We found that the reaction not takes place without substituent group in?-position of amino acid.However,the excellent yield was obtained when one or two methyl groups in?-position of amino acid.The present protocol shows excellent functional group tolerance and provides an efficient method for the synthetic of aryl sulfonamides in excellent yields.?b?Copper-promoted C-N bond cleavage cleavage for the synthesis of primary aryl amidesSimilarly,a novel protocol for CuCl₂ promoted oxidative C-N bond cleavage of N-benzoyl amino acids was developed by using benzoylamino acids as substrates,copper chloride as an oxidant,and DMSO as solvent at 120?for 11 h.The present protocol also shows good functional group tolerance and provides an alternative method for the synthetic of primary aryl amides in excellent yields.On the basis of the results obtained and previous reports,a plausible reaction mechanism is proposed...