Organoiodine(V) Reagents in Organic Synthesis

Abstract

Organohypervalent iodine reagents have attracted significant recent interest as versatile and environmentally benign oxidants with numerous applications in organic synthesis. This Perspective summarizes synthetic applications of hypervalent iodine(V) reagents: 2-iodoxybenzoic acid (IBX), Dess-Martin periodinane (DMP), pseudocyclic iodylarenes, and their recyclable polymer-supported analogues. Recent advances in the development of new catalytic systems based on the generation of hypervalent iodine species in situ are also overviewed.

Iodonium ylides in organic synthesis

“…[1][2][3][4][5][6][7][8][9][10] Hypervalent iodine reagents are now widely used in organic synthesis as versatile and sustainable reagents whose chemical properties are similar to the heavy metals derivatives, like mercury(II), thallium(III), lead(IV), osmium(VIII) and chromium(VI), but without the toxicity and environmental problems associated with these metals.…”

Benziodoxol(on)e Reagents as Tools in Organic Synthesis: The Background behind the Discovery at the Laboratory of Catalysis and Organic Synthesis

“…The enhanced stability of heterocyclic hypervalent iodine reagents, especially benziodoxolones derived from 2-iodobenzoic acid, is indeed well-established, and has allowed the isolation of unique reagents, such as trifluoromethyl (Togni reagents 2 and 3) or azido derivatives (benziodoxolone 4). 3 Figure 1: Selected examples of cyclic hypervalent iodine reagents.…”

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.…”