Multi-component Tandem Strategy For Synthesis Of ?-chlorosulfone And Phosphonate Ester Heteroatom Compounds

Heteroatom compounds are important raw materials for organic synthesis,especially,?-haloalkenyl sulfones and phosphonate ester compounds are applied widely to organic synthesis,pharmaceutical,pesticide,materials and other fields.The multi-step synthesis suffers from issues of atomic economy,low cumulative yield,and high energy consumption.The multi-component tandem reactions can overcome these shortcomings.Therefore,it is of great significance and economic value to employ this strategy for preparing functional compounds.In this paper,we introduce the multi-component tandem strategy to efficiently synthesize ?-haloalkenyl sulfones and phosphonate ester compounds.The specific contents and research results come as follows:(1)An atom-economic and one-pot addition of sodium arenesulfinates to either alkynes or alkenes was achieved over iron catalysis,regio-and stereo-selectively producing ?-haloalkenyl and ?-chloroalkyl sulfones in moderate to good yields.Compared with the reported methods,this method has many advantages:simple conditions,short reaction time,wide substrate scope and easy product-derivatization.In this reaction,ferric chloride acts as chlorine source and oxidant.The final product structure was determined by X-ray analysis.A plausible mechanism was proposed on the basis of XPS analysis and control experiments.(2)Together with a base,dibromomethane enables the efficient synthesis of organic phosphonates from P(O)-OH compounds and commercially available amines via multi-component tandem strategy.It was the first time to report the method that amines provided a carbon source by cleavage of C-N bonds.Based on control experiments,we proposed a plausible mechanism for the reaction.