Exploration of Solvent‐Controlled Reactive Intermediates in the Synthesis of Aryloselenazoles: Altered Chalcogen Bonding Interactions

A solvent-controlled synthesis process has been developed for the preparation of a wide spectrum of functional 2-aryl-aryloselenazoles. Investigation on reactive intermediates through theoretical studies helped establish the possible mechanism of the present approach. Interestingly, the current strategy allows the synthesis of star-shaped benzoselenazoles, which are generally synthesized following multistep processes. Careful choice of starting substrates led to the synthesis of organoselenium variants of some possible metal-coordinating ligands having structural similarities with several known ligands in the area of coordination chemistry. The present approach was explored further for gram-scale synthesis of 2-phenyl-benzoselenazole. Moreover, the possible impact of structural aspects particularly remote functionalization in altering the chalcogen bonding interactions (CBIs) at the molecular level in solid-state has been demonstrated. This was established by studying the crystal structures of a few 2-aryl-aryloselenazoles.