Electrochemically-promoted synthesis of benzo[ b ]thiophene-1,1-dioxides via strained quaternary spirocyclization.
Ruitao LiDafu YuanMengqi PingYuyi ZhuShaofei NiMing LiLi-Rong WenLin-Bao ZhangPublished in: Chemical science (2022)
We report an approach for the synthesis of benzothiophene motifs under electrochemical conditions by the reaction of sulfonhydrazides with internal alkynes. Upon the formation of a quaternary spirocyclization intermediate by the selective ipso -addition instead of an ortho -attack, the S-migration process was rationalized to lead to the products. Computational studies revealed the selectivity and the compatibility of drug molecules showcased the potential application of the protocols.