Transition metal-free approach to the direct C–H selenocyanation of 2-iminothiazolines via in situ generated triselenodicyanide

Abstract

Herein, we present an efficient, metal-free method for the C–H selenocyanation of 2-iminothiazoline using readily available selenium dioxide (SeO₂) and malononitrile. The reaction, enabled by the triselenodicyanide generated through the oxidative coupling of malononitrile and selenium dioxide under ambient air conditions and facilitates the electrophilic aromatic substitution in a wide range of substrates. This alternative strategy offers several advantages including mild reaction conditions, avoidance of transition metal catalysts, ligands and oxidants, shorter reaction times, and good to excellent yields. The proposed synthetic protocol tolerates to a broad range of substrates, suitable for gram-scale synthesis, and features operational simplicity with the use of odorless, inexpensive reagents and straightforward purification of the final products.