Journal
ORGANIC CHEMISTRY FRONTIERS
Volume 4, Issue 3, Pages 343-349Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c6qo00588h
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Funding
- Council of Scientific and Industrial Research (CSIR)
- Science and Engineering Research Board (SERB) through a J. C. Bose Fellowship
- University Grants Commission (UGC), New Delhi
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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.
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