Study On The Novel Sulfonylation Of α-halocarbonyl Compounds

Sulfonylation reactions have emerged as a significant tool for construction of C-S bond.Different sulfonylating agents are applyed to corresponding substrates.At present,the reactions about TosMIC as sulfonylating agent through C-S bond cleavage and sulfonylation of α,α-dibromoketons are rare.This thesis focuses on sulfonylation and the main contents are listed as following:（1）Study on Cu-catalyzed sulfonylation with Tos MIC as a sulfonylating agent.TosMIC was hydrolyzed into formamide derivative under the catalysis of Cu（OTf）2.Then,the C-S bond cleavage is accelerated by Cs₂CO₃.The insitu generated sulfonate was finally trapped by α-bromocarbonyl compounds to form β-carbonyl sulfones.Through a series of control experiments,the reaction mechanism was revealed,which may provid direction for later studies.（2）Study on one-pot reduction/sulfonylation of α,α-dibromoketons.In presence of RSO₂ Na,α,α-dibromoketons are reduced to α-bromoketons,which then reacts with RSO2 Na to form α-sulfonylketons in a one-pot form.According to the experiment results,we disclosed the plausible reaction mechanism by the competition experiments.This sulfonylation reaction is free of metal catalyst and results in good to excellent yields for a variety of substrates.