35242-04-7Relevant academic research and scientific papers
Effective oxidation of benzylic and alkane C-H bonds catalyzed by sodium o-iodobenzenesulfonate with Oxone as a terminal oxidant under phase-transfer conditions
Cui, Li-Qian,Liu, Kai,Zhang, Chi
supporting information; experimental part, p. 2258 - 2265 (2011/05/08)
Catalytic oxidation of benzylic C-H bonds could be efficiently realized using IBS as a catalyst which was generated in situ from the oxidation of sodium 2-iodobenzenesulfonate (1b) by Oxone in the presence of a phase-transfer catalyst, tetra-n-butylammonium hydrogen sulfate, in anhydrous acetonitrile at 60 °C. Various alkylbenzenes, including toluenes and ethylbenzenes, several oxygen-containing functionalities substituted alkylbenzenes, and a cyclic benzyl ether could be efficiently oxidized. And, the same reagent system of cat. 1b/Oxone/cat. n-Bu4NHSO4 could be applied to the effective oxidation of alkanes as well.
Iodine(V) reagents in organic synthesis. Part 4. o-Iodoxybenzoic acid as a chemospecific tool for single electron transfer-based oxidation processes
Nicolaou,Montagnon,Baran,Zhong
, p. 2245 - 2258 (2007/10/03)
o-Iodoxybenzoic acid (IBX), a readily available hypervalent iodine(V) reagent, was found to be highly effective in carrying out oxidations adjacent to carbonyl functionalities (to form α, β-unsaturated carbonyl compounds) and at benzylic and related carbon centers (to form conjugated aromatic carbonyl systems). Mechanistic investigations led to the conclusion that these new reactions are initiated by single electron transfer (SET) from the substrate to IBX to form a radical cation which reacts further to give the final products. Fine-tuning of the reaction conditions allowed remarkably selective transformations within multifunctional substrates, elevating the status of this reagent to that of a highly useful and chemoselective oxidant.
Modulation of the reactivity profile of IBX by ligand complexation: Ambient temperature dehydrogenation of aldehydes and ketones to α,β-unsaturated carbonyl compounds
Nicolaou,Montagnon, Tamsyn,Baran, Phil S.
, p. 993 - 996 (2007/10/03)
The reactivity profile of IBX can be altered by complexation with various ligands (e. g. 1-4). A new complex, IBX·MPO, is a remarkably effective oxidant and allows the room-temperature dehydrogenation of carbonyl compounds, for example, the formation of cyclooctenones 6 and 7 from cyclooctanone 5. IBX = iodoxybenzoic acid; MPO = 4-methoxypyridine-N-oxide.
