电化学促进的苯并[]噻吩-1,1-二氧化物的合成——应变季碳螺环化反应
Electrochemically-promoted synthesis of benzo[]thiophene-1,1-dioxides strained quaternary spirocyclization.
作者信息
Li Ruitao, Yuan Dafu, Ping Mengqi, Zhu Yuyi, Ni Shaofei, Li Ming, Wen Lirong, Zhang Lin-Bao
机构信息
State Key Laboratory Base of Eco-Chemical Engineering, College of Chemistry and Molecular Engineering, Qingdao University of Science & Technology Qingdao 266042 P. R. China
Department of Chemistry, Shantou University Shantou Guangdong 515063 P. R. China.
出版信息
Chem Sci. 2022 Jul 28;13(34):9940-9946. doi: 10.1039/d2sc01175a. eCollection 2022 Aug 31.
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 -addition instead of an -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.
我们报道了一种在电化学条件下通过磺酰肼与内炔反应合成苯并噻吩基序的方法。通过选择性的 - 加成而非 - 进攻形成季螺环化中间体后，S - 迁移过程被认为会导致产物的生成。计算研究揭示了选择性，并且药物分子的兼容性展示了该方法的潜在应用。
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