Stabilized 2-Iodoxybenzoic Acid (SIBX)

Selective demethylation reactions of biomass-derived aromatic ether polymers for bio-based lignin chemicals

“…53 While stabilized 2-iodoxybenzoic acid has significant improvements compared with its unstabilized counterpart, which has explosive properties, it is still a strong oxidizing agent that needs to be handled cautiously and has to be deactivated before disposal. 54 Moreover, IBX poses considerably hazards to human health and is used typically in combination with tetrahydrofuran, which is also considered a problematic solvent primarily due to health concerns. 32 Thus, while the demethylation reaction with IBX is highly selective and good yields can be obtained, this approach is also found particularly wanting in terms of health, safety and environmental aspects and required further improvements in that regard.…”

ortho‐Quinols in (Bio)Synthesis of Natural Products

“… [9b] Much later, our own contribution to the total synthesis of natural non‐dimerizing ortho ‐quinols started with that of (+)‐wasabidienone B 1 ( 6 ). An hydroxylative phenol dearomatization (HPD) was performed on the phloroglucinolic phenol enantiomer ( R )‐ 56 in THF at room temperature using the hypervalent iodine‐based reagent SIBX (i.e., stabilized IBX, see Section 3.4, Figure 8) [34a,b] . The resulting 1 : 1 diastereomeric mixture was then separated by semi‐preparative HPLC to furnish pure (+)‐ 6 [34c] .…”

“…In 2007, we reported the first chemical synthesis of the bicyclo[2.2.2]octenone‐containing bissesquiterpenoid (+)‐aquaticol ( 22 , Figure 3). [47] We had also relied on an oxygenating phenol dearomatization process as the key step of this synthesis, but we used the λ 5 ‐iodane SIBX (Figure 8) [34a,b] as an oxygen‐atom transfer reagent to convert (+)‐hydroxycuparene ( 23 b , syn . cuparenol) into the diastereomeric mixture of ortho ‐quinols 23 a and 23 c , which led to a 1 : 1 mixture of (+)‐ 22 and the diastereomeric [4+2] cycloadduct 112 (Scheme 21).…”