Catalyst-Free and Solvent-Controlled Divergent Synthesis of Difluoromethylene-Containing <i>S</i>-Heterocycles
Jun‐Xiong He, Zhihao Zhang, Bo‐Shuai Mu, Xiao‐Yuan Cui, Jian Zhou, Jin‐Sheng Yu
Abstract
An unprecedented catalyst-free reaction of benzo[b]thiophene-2,3-diones with difluoroenoxysilanes has been developed using either MeOH or H2O as the solvent, which constitutes a facile and efficient protocol for the solvent-controlled divergent synthesis of five- and seven-membered S-heterocycles featuring a gem-difluoromethylene group. A gram-scale synthesis and the diversification of the product transformations to other difluorinated S-heterocycles further highlight its utility.
Topics & Concepts
ChemistryCatalysisThiopheneSolventCombinatorial chemistryOrganic chemistryDivergent synthesisFluorine in Organic ChemistrySulfur-Based Synthesis TechniquesSynthesis and Biological Evaluation