Structurally Diverse Synthesis of Five-, Six-, and Seven-Membered Benzosultams through Electrochemical Cyclization
Aiyun Liu, Tiantian Guo, Shuangshuang Zhang, Shuangshuang Zhang, Han Yang, Qi Zhang, Yonghai Chai, Shengyong Zhang, Shengyong Zhang
Abstract
We have developed a metal- and oxidant-free approach to structurally diverse synthesis of benzosultams from aryl sulfonamides through an electrochemical cyclization. Upon variation of the ortho substituent on aryl sulfonamides, five-, six-, and seven-membered benzosultams were efficiently assembled in an atom- and resource-economic manner. The generality of the process is demonstrated by the formation of five- to seven-membered cyclic products from 42 substrates bearing substituents with different electronic effects and steric hindrance.
Topics & Concepts
Steric effectsChemistrySubstituentArylElectrochemistryCombinatorial chemistryAtom (system on chip)Electronic effectStereochemistryOrganic chemistryComputer scienceAlkylPhysical chemistryElectrodeEmbedded systemSulfur-Based Synthesis TechniquesRadical Photochemical ReactionsCatalytic C–H Functionalization Methods