Ligand exchange of aryl iodine dicarboxylates to form reagents with differing solubilities

Abstract

Hypervalent iodine (HVI) reagents are employed in organic synthesis as versatile, proficient, and environmentally friendly reagents. Despite the utility of such reagents, the application of HVI reagents, especially phenyliodonium diacetate (PIDA), has been limited due to its poor solubility in a myriad of solvents. The aggregated and polymeric structures of many HVI reagents account for their poor solubility, thus limiting the reactivity and use of HVI reagents in reactions in non-polar solvents. The research presented herein outlines ligand exchange reactions of universal carboxylic acids promoted by phenyliodonium diacetate (PIDA) reagents, in which the acetate moiety of PIDA is modified, ultimately enhancing the solubility and reactivity of HVI reagents.

Introduction to hypervalent iodine chemistry. Part 3

“…Part 1 (2020) and Part 2 (2021) contain total 20 papers covering a broad range of topics of the HI chemistry. Specific topics of these papers include the following: theoretical and computational studies of HI compounds, [2][3][4] structural studies, 5 development of new synthetic approaches to HI reagents, [6][7][8][9] photochemical reactions involving HI chemistry, 10,11 industrial applications of hypervalent polyiodides, 12 and numerous synthetic applications of HI reagents. [13][14][15][16][17][18][19][20] Part 3 of the HI series will be published in 2022 covering all topics of iodine chemistry involving hypervalent species and halogen bonding.…”