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The oxidative dearomatization of resorcinol derivatives, which are outfitted with a lactic acid derived chiral tether, and mitigated by hypervalent iodine derivatives of PhIO, affords stable chiral cyclohexadienones as useful building blocks for the construction of many highly functionalized...
Several transition metal-mediated oxidations using hypervalent iodine species are reported. A convenient procedure for preparation of iodylarenes via RuCl 3 -catalyzed oxidation of iodoarenes has been developed. This procedure allows the generation of highly reactive monomeric iodine(V) species,...
Both λ 3 - and λ 5 -iodanes have proven to be useful reagents in the oxygenative dearomatization of phenols, and exploitations of their chemistry in the conception of both substrate- and reagent-controlled asymmetric variants of such a transformation of great value for natural product synthesis...
The addition of the hypervalent iodine reagent PIFA (phenyliodine(III) bis(trifluoroacetate)) to a series of properly substituted N -(3-aminopropyl)alkynylamides results in the efficient formation of a functionalized 5-aroyl-2-pyrrolidinone skeleton. By proper manipulations of the...
The synthesis and characterization of new hypervalent iodine reagents ArINTs ( 2a ), ArIO ( 3a ), and ArIO 2 ( 4a ) (Ar=2- tert -butylsulfonyl-5- tert -butylphenyl) are described. These reagents are compared to previously reported analogous set of reagents Ar=2- tert -butylsulfonylphenyl and...
Functionalized bicyclo(3.3.1)non-3-en-2-ones are obtained from commercially available phenols by a hypervalent iodine oxidation, enone epoxidation, epoxide thiolysis, and intramolecular aldol reaction sequence. Reaction optimization studies identified room temperature as well as...
Several new five- and a six-membered heterocyclic monochloroiodanes, including two cationic species, were synthesized. Three of which were used for the preparation of corresponding trifluoromethylation reagents. These compounds were characterized by X-ray crystallography for a comparative...
We first introduced 1,1,1,3,3,3-hexafluoroisopropanol (HFIP) and 2,2,2-trifluoroethanol (TFE) as unique solvents for reactions involving hypervalent iodine-mediated phenolic oxidations in the 1980s, in which the fluoroalcohols have been successfully utilized as stabilizing solvents of the...
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