Redox‐Divergent Construction of (Dihydro)thiophenes with DMSO
Heng Liu, Gu‐Cheng He, Chaoyang Zhao, Xiang‐Xin Zhang, Ding‐Wei Ji, Yan‐Cheng Hu, Qing‐An Chen
Abstract
Thiophene-based rings are one of the most widely used building blocks for the synthesis of sulfur-containing molecules. Inspired by the redox diversity of these features in nature, we demonstrate herein a redox-divergent construction of dihydrothiophenes, thiophenes, and bromothiophenes from the respective readily available allylic alcohols, dimethyl sulfoxide (DMSO), and HBr. The redox-divergent selectivity could be manipulated mainly by controlling the dosage of DMSO and HBr. Mechanistic studies suggest that DMSO simultaneously acts as an oxidant and a sulfur donor. The synthetic potentials of the products as platform molecules were also demonstrated by various derivatizations, including the preparation of bioactive and functional molecules.