Synthesis and oxidation reactions of a user- and eco-friendly hypervalent iodine reagent

Hypervalent Iodine Reagents for the Oxidation of Alcohols and Their Application to Complex Molecule Synthesis

“…[15] mIBX (3) selectively oxidizes benzylic and allylic alcohols to the corresponding ketones and aldehydes in water, while non-allylic/ benzylic alcohols cannot be oxidized. An important aspect of this oxidation protocol is the near insolubility of 14, the reduced form of 3.…”

Tetrafluoro‐IBA and‐IBX: Hypervalent Iodine Reagents

“…It has been reported to be explosive, [6] it has low solubility so it is often limited to use in polar solvents such as DMSO, [3][4][5] and the conditions for many of the IBX-mediated reactions often involve high temperatures. Some attempts-such as the addition of additives to IBX (2) for its stabilization [7] or for increasing the reactivity, [4] the functionalization of the arene moiety to improve solubility in organic solvents [8] or water, [9] and the attachment to a solid support [10] -have solved some of these problems but rarely all of them. Theoretical investigations to improve reactivity have also been published.…”

2‐Iodoxybenzoesäure – ein einfaches Oxidationsmittel mit einer Vielfalt an Anwendungsmöglichkeiten

“…Benzylische und allylische Alkohole konnten durch mIBX in Wasser oder wässrigem THF effektiv oxidiert werden. [33] Eine etwas größere Anwendungsbreite zeigte das Isomer 8, das in wässrigem DMF ähnliche Reaktivität bezüglich der Oxidation von Alkoholen besitzt wie IBX. [34] In anderen wässrigen Lösungsmittelge-mischen verläuft die Reaktion allerdings weniger sauber.…”