有機合成化学協会誌
Online ISSN : 1883-6526
Print ISSN : 0037-9980
ISSN-L : 0037-9980
総説および総合論文
ハロゲンをLewis酸中心として活用する高選択的有機変換反応の開発
石原 一彰
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ジャーナル 認証あり

2014 年 72 巻 2 号 p. 137-148

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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.

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