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Title: New Isoxazole‐Substituted Aryl Iodides: Metal‐Free Synthesis, Characterization and Catalytic Activity
Abstract A series of new isoxazole‐substituted aryl iodides1 a–1 dhave 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 oximes5 a–5 d. Structure of the synthesized aryl iodides1were characterized by IR,1H NMR,13C NMR and HRMS. The structure of1 awas also confirmed by single‐crystal X‐ray crystallography. Further, catalytic activity of iodoarenes1 a–1 dwas screened for the oxidation of hydroquinones and sulfides. On oxidation using aryl iodides1withm‐CPBA as terminal oxidant, hydroquinones afforded benzoquinones while sulfides gave corresponding sulfoxides in good to excellent yields. Iodoarene1 bshowed the best catalytic activity for the oxidation of sulfides and hydroquinones. Moreover, iodoarene1 b, was also utilized for α‐oxytosylation of acetophenones.  more » « less
Award ID(s):
2243793
PAR ID:
10497978
Author(s) / Creator(s):
; ; ;
Publisher / Repository:
Wiley
Date Published:
Journal Name:
European Journal of Organic Chemistry
Volume:
27
Issue:
5
ISSN:
1434-193X
Format(s):
Medium: X
Sponsoring Org:
National Science Foundation
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