Regioselective 1,2-Alkoxy, Hydroxy, and Acetoxy Iodination of Alkenes with I2 Catalyzed by Ce(SO3CF3)4

Nitrogen Dioxide‐Catalyzed Electrophilic Iodination of Arenes

“…One of the most effective solutions to this situation is the use of iodonium equivalents (I + ), for example, N-iodosuccinimide, [7] Niodosaccharin, [8] iodine monochloride [9] and IOAc. [10] Another effective solution is the oxidative activation strategy where the electrophilic I + -type species is generated through oxidation of iodine sources by oxidizing reagent systems, for example, CrO 3 , [11] PbA C H T U N G T R E N N U N G (OAc) 4 , [12] CeA C H T U N G T R E N N U N G (OTf) 4 , [13] hydrogen peroxide, [14] H 5 IO 6 , [15] peroxodisulfate salts, [16] and ferrate salts. [17] The use of molecular oxygen as the oxidant is a still desirable goal from environmental and economic perspectives.…”

Potassium 4-Iodylbenzenesulfonate (PIBS): An Efficient Recyclable Hypervalent Iodine Reagent for Iodo-functionalization of Alkenes, Alkynes and Ketones

“…Our procedure for iodomethoxylation of alkenes allows simple and environmentally sustainable synthesis of important products 3 in high yields ( Table 1). Previously known methods for the preparation of -iodoethers 3 were based on the reactions of alkenes with non-recyclable reagents: N-iodosuccinimide [38][39][40], dichloroiodoisocyanuric acid [41], triiodoisocyanuric acid [42] N-iodosaccharin [43], ICl [44], I 2 [45], t-butyl or methyl hypoiodites [46], I(Py) 2 BF 4 [47], iodide/iodate [48], I 2 -H 2 O 2 [49], AgOTf [50], Ce (IV) salts [51], thallium salts [52,53], Pb (IV) salts [54], Cu (II) salts [55,56], and Hg (II) salts [57].…”

Iodine

“…65 In the presence of Ce (IV) triflate, alkenes react with I 2 and an alcohol to give the iodohydrin. 66 Cyclohexene reacts with methanol and iodine, for example eq 34, to give an 80% yield of transmethoxyiodocyclohexane. In the absence of Ce(OTf) 4 , the reaction gave only 10% of product after 5 days.…”