Brønsted Acid Promoted Sulfenylacyloxylation of Alkynes: Access to 4‐Sulfenylisocoumarins
Arijit Saha, E. Ramesh, Akhila K. Sahoo
Abstract
Abstract Presented herein is the Brønsted acid (MsOH) mediated electrophilic sulfenylacyloxylation of o ‐alkynylbenzoates via alkyne activation by in‐situ formed sulfonium cations from bench‐stable N ‐thioaryl/alkyl‐succinimides followed by the intramolecular regioselective cyclization. The transformation provides access to structurally diverse 4‐sulfenylisocoumarins in 77–98% yields with broad functional group compatibility. The reaction scalability and reusability of phthalimide protecting group make this protocol synthetically viable. magnified image
Topics & Concepts
ChemistrySulfoniumIntramolecular forcePhthalimideBrønsted–Lowry acid–base theoryRegioselectivityElectrophileAlkyneCombinatorial chemistryFunctional groupAlkylReusabilityOrganic chemistryMedicinal chemistryCatalysisProgramming languageSalt (chemistry)PolymerComputer scienceSoftwareSulfur-Based Synthesis TechniquesCatalytic C–H Functionalization MethodsChemical Synthesis and Reactions