Me<sub>3</sub>SiCl‐Catalyzed Electrophilic Thiocyanation/Cyclization of Alkynylbenzoates to Synthesize 4‐Thiocyanatoisocourmarins
Chukai Shao, Ying He, Hongquan Yin, Fu‐Xue Chen
Abstract
Abstract A metal‐free and regioselective electrophilic thiocyanation/cyclization of alkynylbenzoates has been developed to afford series of thiocyanato‐containing isocourmarins catalyzed by Me 3 SiCl. Tandem thiocyanation/6‐ endo cyclization of alkynylbenzoates was achieved using N ‐thiocyanatosuccinimide (NTS). A wide scope of substrates and functional groups have been tolerated with moderate to excellent yield up to 98%. The mild reaction conditions make this protocol more practical to access isocourmarins bearing a thiocyanato group with diverse transformations.
Topics & Concepts
ChemistryElectrophileRegioselectivityCatalysisYield (engineering)Reaction conditionsCombinatorial chemistryFunctional groupTandemMedicinal chemistryOrganic chemistryMaterials scienceMetallurgyPolymerComposite materialSulfur-Based Synthesis TechniquesCatalytic C–H Functionalization MethodsSynthesis and Catalytic Reactions