2‐Iodoxybenzoic Acid—A Simple Oxidant with a Dazzling Array of Potential Applications

Abstract

Since its discovery by Christoph Hartmann and Victor Meyer in 1893, 2-iodoxybenzoic acid (IBX) has emerged as a rather ubiquitous oxidant for organic synthesis. The past decade has seen the development of a large variety of applications that go far beyond the simple oxidation of alcohols. This Review is concerned with the synthetic potential of IBX, with particular emphasis on uncommon reactivity patterns and novel fields of application.

Glycosylation Reaction of <i>Thioglycosides</i> by Using Hypervalent Iodine(III) Reagent as an Excellent Promoter

“…16,17) Nowadays, the environmentally-benign hypervalent iodine oxidation has witnessed significant progress in the field of organic chemistry. [18][19][20][21][22][23][24][25][26][27][28][29][30] We have been engaged in the development of the oxidation of the sulfur atom utilizing hypervalent iodine reagents to form an active iodonium intermediate. 31,32) Thus, we have recently developed novel methods of hypervalent iodine-induced glycosylation of thioglycoside.…”

Preparation and X-ray Structural Study of Dibenziodolium Derivatives

“…The obtained solid was washed with Et 2 O three times and dried in a vacuum to provide dibenziodolium trifluoromethanesulfonate 10 (0.781 g, 91% yield) as a white solid; mp 247−249°C. 1 Preparation of Dibenziodolium Bis(trifluoromethane)sulfonimide (11). To a stirred solution of 2-iodobiphenyl (0.56 g, 0.35 mL, 2.0 mmol) in anhydrous CH 2 Cl 2 (6.0 mL) were added m-CPBA (77%, 0.736 g, 3.2 mmol) and a solution of HNTf 2 (1.26 g, 4.5 mmol) in CH 2 Cl 2 (5.0 mL).…”

The system PhIO/Ph3P as an efficient reagent for mild and direct coupling of alcohols with carboxylic acids

“…Such requirements are often met in the hypervalent iodine reagents, 3 whose chemistry has experienced remarkable growth during the last decades mainly in oxidation processes. [4][5][6][7][8][9][10][11][12][13][14][15][16][17] In the light of these properties of organoiodine reagents, Zhang et al, 18 reported recently a method of broad scope for the coupling of carboxylic acids with amines or alcohols, using the hypervalent iodine lactone 1 as coupling reagent (Scheme 1). Treatment of carboxylic acids with amines or alcohols in the presence of lactone 1, triphenylphosphine and dimethylaminopyridine (DMAP), gave respective amides or esters in high yields.…”