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Electrochemically-promoted synthesis of benzo[b]thiophene-1,1-dioxides via strained quaternary spirocyclization.

ABSTRACT: 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.

SUBMITTER: Li R 

PROVIDER: S-EPMC9431990 | biostudies-literature | 2022 Aug

REPOSITORIES: biostudies-literature

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Electrochemically-promoted synthesis of benzo[<i>b</i>]thiophene-1,1-dioxides <i>via</i> strained quaternary spirocyclization.

Li Ruitao R   Yuan Dafu D   Ping Mengqi M   Zhu Yuyi Y   Ni Shaofei S   Li Ming M   Wen Lirong L   Zhang Lin-Bao LB  

Chemical science 20220728 34

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 <i>ipso</i>-addition instead of an <i>ortho</i>-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  ...[more]

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