Transition-Metal-Free HFIP-Mediated Organo Chalcogenylation of Arenes/Indoles with Thio-/Selenocyanates
Pratibha Kalaramna, Avijit Goswami
Abstract
We have developed a protocol for the synthesis of diaryl thio-/selenoethers by the reaction of aryl chalcogenocyanates with electron rich arenes/hetero arenes via HFIP promoted C–H activation. The reaction produces chalcogenides in good to excellent yields under mild conditions without the need of a transition metal as a catalyst. The HFIP-mediated reactions tolerated a wide range of functional groups and set the stage for the synthesis of diversely decorated chalcogenides. A mechanism involving activation of the C–H bond through hydrogen bonding is proposed.
Topics & Concepts
ChemistryThio-CatalysisArylTransition metalCombinatorial chemistryHydrogen bondReaction conditionsPhotochemistryMedicinal chemistryOrganic chemistryMoleculeAlkylSulfur-Based Synthesis TechniquesOrganoselenium and organotellurium chemistryChemical Synthesis and Reactions