Nickel-Catalyzed Denitrogenative Cyclization of 1,2,3,4-Benzothiatriazin-1,1(2<i>H</i>)-dioxides with Arynes To Synthesize Biaryl Sultams
Vijaykumar H. Thorat, Yu‐Lin Tsai, Yong-Ran Huang, Chien‐Hong Cheng, Jen‐Chieh Hsieh
Abstract
Herein, we report the nickel-catalyzed denitrogenative cyclization reaction of 1,2,3,4-benzothiatriazine-1,1-dioxides with arynes to generate the polysubstituted biaryl sultams with tolerance of a wide diversity of substituents on every subunit. The mechanistic study indicates that the reaction is initiated by the formation of a diradical species, which reacts with a nickel complex to form a nickelacycle intermediate and carries out the subsequent cyclization through insertion of an aryne.
Topics & Concepts
AryneDiradicalChemistryCatalysisNickelCombinatorial chemistryMedicinal chemistryStereochemistryOrganic chemistryExcited statePhysicsNuclear physicsSinglet stateCyclization and Aryne ChemistryChemical synthesis and alkaloidsCatalytic Alkyne Reactions