Copper-Catalyzed Reductive Coupling Of Aryl Sulfonyl Chlorides With H-Phosphonates Leading To S-Aryl Phosphorothioates

In this thesis, copper-catalyzed reductive coupling of aryl sulfonyl chlorides withH-phosphonates leading to S-aryl phosphorothioates has been developed. The mainresults obtained are as follows:1. Phosphorothioate has proven to be a useful skeleton in organic synthesis as avaluable building block, in pharmaceuticals and pesticides due to its biological andphysical properties. Some problems exit with these procedures reported in theliteratures, such as:1) requirement of the complicated or foul odor starting material,which are not commercially available;2) narrow scope of substrates. The remainingchallenge is to develop a general and applicable strategy for a variety of S-arylphosphorothioates. Therefore, we focus our current research interests on buildingsuch a structure. We have developed an efficient protocol for copper-catalyzed directcross-coupling of aryl sulfonyl chlorides with H-phosphonates. The various S-arylphosphorothioates were afforded in up to86%yield for20examples. The ratio ofsubstrates played an important role in this reaction. This protocol features highefficiency, wide functional groups tolerance, commercially aryl sulfonyl chlorides asstarting materials and base-free conditions.2. A plausible reaction mechanism was proposed according to the literatures andresults obtained as follows:...