Synthesis of thioesters using an electrochemical three-component reaction involving elemental sulfur
Gongbo Liu, Shuoyu Xu, Yangyang Yue, Changhui Su, Wangze Song
Abstract
An electrochemical three-component reaction involving elemental sulfur is disclosed for achieving a metal-free, oxidant-free synthesis of thioesters in a high atom-economical, step-economical and chemoselective manner. A mechanistic investigation indicates that the use of elemental sulfur to trap acyl radical derived from radical umpolung of α-keto acid with an electrochemical design can efficiently generate a carbonyl thiyl radical, which can further be captured by diazoalkane to afford various thioesters.
Topics & Concepts
SulfurElectrochemistryComponent (thermodynamics)ChemistryCombinatorial chemistryInorganic chemistryOrganic chemistryElectrodePhysical chemistryThermodynamicsPhysicsSulfur-Based Synthesis TechniquesMulticomponent Synthesis of HeterocyclesOrganic Chemistry Cycloaddition Reactions