Conversion of Alcohols to Alkyl Aryl Sulfides by a New Type of Oxidation-Reduction Condensation Using Phenyl Diphenylphosphinite

被引：19

作者：

Kuroda, Kiichi ^{[1
]}

Maruyama, Yuji ^{[2
]}

Hayashi, Yujiro ^{[1
]}

Mukaiyama, Teruaki ^{[3
]}

机构：

[1] Tokyo Univ Sci, Fac Engn, Dept Ind Chem, Shinjuku Ku, Tokyo 1628601, Japan

[2] Tokyo Univ Sci, Fac Sci, Dept Appl Chem, Shinjuku Ku, Tokyo 1628601, Japan

[3] Kitasato Univ, Ctr Basic Res, Kita Ku, Tokyo 1140003, Japan

来源：

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN | 2009年 / 82卷 / 03期

基金：

日本学术振兴会;

关键词：

AZA-WITTIG REACTION; EFFICIENT METHOD; MITSUNOBU REACTION; TERTIARY ALCOHOLS; DIETHYL CYANOPHOSPHONATE; STEREOSPECIFIC SYNTHESIS; STEREOCHEMICAL COURSE; STAUDINGER LIGATION; CONVENIENT METHOD; NATURAL-PRODUCTS;

D O I：

10.1246/bcsj.82.381

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Preparation of alkyl aryl sulfides from alcohols and arenethiols Such as 2-sulfanyl-1,3-benzothiazole (BtzSH) is described by a new type of oxidation-reduction condensation using phenyl diphenylphosphinite (PhOPPh2) and benzoquinone derivatives or azide compounds. This reaction proceeds under mild and neutral conditions and is applicable to the thioetherification of various alcohols in which the chiral secondary and tertiary alcohols are converted into the corresponding chiral sulfides with almost complete inversion of configuration.

引用

页码：381 / 392

页数：12

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