New Isoxazole‐Substituted Aryl Iodides: Metal‐Free Synthesis, Characterization and Catalytic Activity

Abstract

AbstractA series of new isoxazole‐substituted aryl iodides 1 a–1 d have been synthesized by DIB‐mediated [3+2] cycloaddition reaction of 2‐iodo‐1,3‐bis(prop‐2‐yn‐1‐yloxy) benzene (4) with corresponding benzaldehyde oximes 5 a–5 d. Structure of the synthesized aryl iodides 1 were characterized by IR, 1H NMR, 13C NMR and HRMS. The structure of 1 a was also confirmed by single‐crystal X‐ray crystallography. Further, catalytic activity of iodoarenes 1 a–1 d was screened for the oxidation of hydroquinones and sulfides. On oxidation using aryl iodides 1 with m‐CPBA as terminal oxidant, hydroquinones afforded benzoquinones while sulfides gave corresponding sulfoxides in good to excellent yields. Iodoarene 1 b showed the best catalytic activity for the oxidation of sulfides and hydroquinones. Moreover, iodoarene 1 b, was also utilized for α‐oxytosylation of acetophenones.