2014 Volume 72 Issue 2 Pages 137-148
Highly selective organic transformation reactions using halogen Lewis acids are described here. 2-Iodobenzenesulfonic acid has been found to be effective as a precursor of iodine(V) catalyst for the selective oxidation of alcohols and phenols in the presence of Oxone® as a cooxidant. C2-Symmetric iodoarenes bearing conformationally flexible chiral secondary amido groups have been developed as precursors of iodine(III) catalysts for the enantioselective dearomatization of 1-hydroxynaphthyl carboxylic acids and hydroxyphenyl carboxylic acids in the presence of m-chloroperbenzoic acid (mCPBA) as a cooxidant. Chiral quaternary ammonium iodide has been developed as a precursor of iodine(I) catalyst for the enantioselective dehydrogenative carbon-oxygen coupling reaction in the presence of hydrogen peroxide or tert-butyl hydroperoxide (TBHP). Several chiral phosphorous compounds have been developed as chiral nucleophilic base catalysts for the biomimetic enantioselective iodocyclization, bromocyclzation, and protocyclization of polyprenoids. These phosphorous compounds activate N-halosuccinimides (NIS, NBS) and sulfonic acids as halonium salts and protic salts, respectively.
