Oxidations of alkenes with hypervalent iodine reagents: an alternative ozonolysis of phenyl substituted alkenes and allylic oxidation of unsubstituted cyclic alkenes

Advances in Synthetic Applications of Hypervalent Iodine Compounds

“…Iodylbenzene 528 can cleave the unsaturated carbon−carbon double bonds to give the corresponding carbonyl compounds. 1356 For example, the reaction of cyclic compounds 530 with iodylbenzene 528 leads to the oxidative carbon− carbon double bond cleavage affording carbonyl compounds 531 in good yields (Scheme 155). This cleavage reaction probably proceeds via a radical pathway.…”

A divergent approach for the synthesis of (hydroxymethyl)furfural (HMF) from spent aromatic biomass-derived (chloromethyl)furfural (CMF) as a renewable feedstock

“…21 In organic chemistry, they are frequently used for the development of green methodologies for various oxidative transformations. [22][23][24][25][26][27] Hypervalent iodine reagents have been prospected for selective oxidation of benzylic halides to corresponding carbonyl compounds in good yields. However, oxidative transformation of CMF to corresponding alcohol (HMF) in good yields is not realized so far under mild one pot reaction condition using hypervalent iodine reagents.…”

Selective Hydroperoxygenation of Olefins Realized by a Coinage Multimetallic 1‐Nanometer Catalyst

“…We evaluated the catalytic reactivity of the multimetallic SNPs by using cyclohexene as a model substrate, which is one of the important C6 compounds in the chemical industry [24, 25] . Although many studies of the catalytic oxidation reaction of cyclohexene have been reported especially for the NP catalysts, they have required severe reaction conditions such as high temperature, high pressure, use of strong oxidants, and addition of initiators [26–30] . In this study, using the highly reactive SNP catalysts, we newly investigated this reaction under the very mild condition at low temperature, at atmospheric pressure, with molecular oxygen as a weak oxidant, and without initiators.…”

“…[24,25] Although many studies of the catalytic oxidation reaction of cyclohexene have been reported especially for the NP catalysts, they have required severe reaction conditions such as high temperature, high pressure, use of strong oxidants, and addition of initiators. [26][27][28][29][30] In this study, using the highly reactive SNP catalysts, we newly investigated this reaction under the very mild condition at low temperature, at atmospheric pressure, with molecular oxygen as a weak oxidant, and without initiators. First, as monometallic and bimetallic SNPs, Au 28 /KB, Ag 28 /KB, Cu 28 /KB, Au 12 Ag 16 /KB, Au 12 Cu 16 /KB, and Ag 12 Cu 16 /KB were also synthesized by the same method for trimetallic Au 4 Ag 8 Cu 16 /KB as already described.…”