A practical protocol has been developed for asymmetric cis-dihydroxylation of electron-deficient alkenes with Oxone catalysed by a manganese complex bearing a chiral tetradentate N(4)-donor ligand affording cis-diols in up to 95% yield with up to 96% ee. Analysis of the reaction mixture by high resolution ESI-MS revealed the formation of a cis-dioxomanganese(V) intermediate.

A safe and convenient protocol was developed for in situ generation of various dichlorinating agents (cf. Cl2, NCl3, Et4NCl3, ArICl2) from oxone and chloride. The synthetic utility of this protocol was demonstrated by diastereoselective dichlorination of a series of allylic and homoallylic alcohol derivatives with excellent yields and diastereoselectivity.

A recent report has indicated that the oxidizing agent Oxone does not possess the ability to cleave the 2,3-carbon-carbon bond of indole. Work in our laboratory shows that this is not the case. Indole and a variety of aryl ring substituted derivatives readily react to form synthetically important isatoic anhydrides.

Organosulphur compounds can be easily and selectively oxidized to sulfones using a small excess of Oxone(®) (1.6 eq.) under solventless mechanical milling conditions. This green procedure has been efficiently applied to a series of model compounds and to the desulphurization of medium/high sulphur content paraffins (up to 3000 mg kg(-1)).

Recent investigations have shown the oxone-mediated oxidative methyl esterification of benzaldehyde derivatives using methanol. The reactions were accelerated in the presence of indium(III) triflate, a trivalent indium reagent, in many cases. Based on this method of methyl esterification of benzaldehyde derivatives, we further explored an application to heterocyclic aldehydes. The reactions wer...

Biacetyl reacts with oxone to give bis-dioxirane [3,3'-dimethyl-3,3'-bidioxirane, 3B] and mono-dioxirane [1-(3-methyl-dioxiran-3-yl)ethanone, 3A)]. Bis-dioxirane 3B is formed when two oxygens are incorporated into biacetyl, while mono-dioxirane 3A incorporated only one. A greater stability is observed in 3B compared to 3A, which is attributed to an alpha-dioxiranyl (anomeric) effect in the form...

The direct oxidative coupling reaction has been an attractive tool for environmentally benign chemistry. Reported herein is that the hypervalent iodine catalyzed oxidative metal-free cross-coupling reaction of phenols can be achieved using Oxone as a terminal oxidant in 1,1,1,3,3,3-hexafluoropropan-2-ol (HFIP). This method features a high efficiency and regioselectivity, as well as functional-g...

The first synthesis of the fungal natural product (-)-xylariamide A 1 is reported. N,Obis(trimethylsilyl)acetamide induced coupling of D-tyrosine with (E)-but-2-enedioic acid 2,5dioxo-pyrrolidin-1-yl ester methyl ester 5 produced the dechloro natural product 6, which was subsequently monochlorinated using oxone and KCl to yield synthetic 1. (-)Xylariamide A 1, (+)-xylariamide A 2 and (-)-dechlo...