Asymmetric catalytic nitrooxylation and azidation of β-keto amides/esters with hypervalent iodine reagents

Chiral Lewis acid-catalyzed enantioselective nitrooxylation of cyclic and acyclic β-keto amides/esters with hypervalent iodine(III) reagents is reported. A number of α-nitrooxy-β-keto amides/esters were obtained with good yields and high enantioselectivities...

Sterically crowded 1,4-diiodobenzene as a precursor to difunctional hypervalent iodine compounds

Oxidation of a 1,4-di-iodobenzene having four adjacent p-tBu-C6H4 group (Ar′) substituents (1) yields the hypervalent iodine compound 1,4-[I(OAc)2]2-2,3,5,6-Ar′4-C6 (2), that undergoes cyclization to produce dicyclic di-iodonium salt (3).

Convenient Synthesis of Benziodazolone: New Reagents for Direct Esterification of Alcohols and Amidation of Amines

Hypervalent iodine heterocycles represent one of the important classes of hypervalent iodine reagents with many applications in organic synthesis. This paper reports a simple and convenient synthesis of benziodazolones by the reaction of readily available iodobenzamides with m-chloroperoxybenzoic acid in acetonitrile at room temperature. The structure of one of these new iodine heterocycles was confirmed by X-ray analysis. In combination with PPh3 and pyridine, these benziodazolones can smoothly react with alcohols or amines to produce the corresponding esters or amides of 3-chlorobenzoic acid, respectively. It was found that the novel benziodazolone reagent reacts more efficiently than the analogous benziodoxolone reagent in this esterification.