Transition-Metal-Free Tandem Cyclization/<i>N</i>-Arylation Reaction: A Method To Access Biaryl Sultam Derivatives via a Diradical Pathway
Vijaykumar H. Thorat, Jen‐Chieh Hsieh, Chien‐Hong Cheng
Abstract
-arylation reaction sequence of an aryne with a 1,2,3,4-benzothiatriazine-1,1-dioxide is reported. This reaction goes through the intramolecular homolytic cyclization to generate an N-H biaryl sultam intermediate, which enables aryne insertion to access diversely functionalized biaryl sultam derivatives with high yields. The mechanism study indicates that homolytic cyclization is executed by a diradical species, initiated from the thermal decomposition of 1,2,3,4-benzothiatriazine-1,1-dioxide to release a nitrogen molecule.
Topics & Concepts
ChemistryDiradicalHomolysisAryneTandemIntramolecular forceRadicalCombinatorial chemistryThermal decompositionMoleculeMedicinal chemistryPhotochemistryStereochemistryOrganic chemistrySinglet statePhysicsMaterials scienceNuclear physicsExcited stateComposite materialCyclization and Aryne ChemistryCatalytic Alkyne ReactionsChemical synthesis and alkaloids