Issue 3, 2017

Mechanochemical catalytic oxidations in the solid state with in situ-generated modified IBX from 3,5-di-tert-butyl-2-iodobenzoic acid (DTB-IA)/Oxone

Abstract

IBX is an indispensable reagent in contemporary organic oxidation chemistry, despite its explosive and insoluble attributes. The latter drawbacks can be overcome if a more reactive modified version of IBX can be generated in situ catalytically. We show that the sterically-crowded reactive I(V) species can be generated catalytically from the precursor 3,5-di-tert-butyl-2-iodobenzoic acid (DTB-IA) in the presence of a terminal oxidant, i.e., Oxone. The highly reactive modified IBX, i.e., I(V) species, generated in situ from DTB-IA in the presence of Oxone under mechanochemical ball milling conditions, permits unprecedented oxidation of alcohols to carbonyl compounds, vicinal diols to oxidative cleavage products, and non-vicinal diols to lactones in the solid state. Indeed, the results constitute first demonstration of catalytic oxidations in the solid state using a modified o-iodobenzoic acid, an I(I) species.

Graphical abstract: Mechanochemical catalytic oxidations in the solid state with in situ-generated modified IBX from 3,5-di-tert-butyl-2-iodobenzoic acid (DTB-IA)/Oxone

Supplementary files

Article information

Article type
Research Article
Submitted
28 Sep 2016
Accepted
30 Nov 2016
First published
01 Dec 2016

Org. Chem. Front., 2017,4, 343-349

Mechanochemical catalytic oxidations in the solid state with in situ-generated modified IBX from 3,5-di-tert-butyl-2-iodobenzoic acid (DTB-IA)/Oxone

A. K. Mishra and J. N. Moorthy, Org. Chem. Front., 2017, 4, 343 DOI: 10.1039/C6QO00588H

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