Hypervalent iodine(V) reagents in organic synthesis

Abstract

This review summarizes the synthetic applications of hypervalent iodine(V) reagents: iodylbenzene, IBX (2-iodoxybenzoic acid), DMP (Dess-Martin periodinane) and pseudocyclic IBX analogs. Application of these reagents allows mild and highly selective oxidative transformations in a facile and environmentally friendly manner.

The mechanochemical synthesis of quinazolin-4(3H)-ones by controlling the reactivity of IBX

“…Their easy availability, high stability, controlled oxidizing ability, and environmentally benign nature make them highly suitable for the development of new synthetic transformations [13–17]. The chemistry of iodine(V) reagents has been well documented in a number of reviews [18–20]. In continuation of our research focus on the development of synthetic methods using iodine-based reagents [21–26], we here report a method for the synthesis of quinazolin-4(3 H )-ones [27–28] (Fig.…”

Highly efficient and extremely simple protocol for the oxidation α-hydroxyphosphonates to α-ketophosphonates using Dess-Martin periodinane

“…A focused literature survey on the use of IBX in the oxidation of alcohols under anhydrous conditions revealed that there were reports on the use of IBX -BTPP combination in the oxidation of alcohols. [38][39][40][41][42][43][44][45] Based upon these studies it was planned to explore this reagent-oxidant combination in the oxidation of 1a. Accordingly, a model reaction was carried wherein a mixture of 1a (1mmol), IBX (0.1 mmol) and BTPP (1 mmol) in dry acetonitrile (5 mL) was stirred under reflux conditions.…”

Practical Synthesis of 2-Iodosobenzoic Acid (IBA) without Contamination by Hazardous 2-Iodoxybenzoic Acid (IBX) under Mild Conditions

“…Although IBAs can be prepared from 2-IBs by existing methods ( Figure 2 ) [ 63 , 64 , 65 , 66 ], the development of a safer and more efficient method for their synthesis is highly desirable. As shown in Figure 2 , IBAs can be further oxidized to pentavalent cyclic hypervalent IBXs [ 67 ], which need to be prevented for the preparation of IBAs [ 68 , 69 , 70 ], mainly due to the explosive nature of IBXs on heating and impact, while IBXs are useful in some small-scale reactions [ 71 , 72 , 73 , 74 , 75 , 76 ]. Thus, contamination by IBX in the IBA products should be avoided for long-term safe storage or large-scale use.…”