One-pot preparation of Julia-Kocienski sulfides and sulfones from alcohols

被引：6

作者：

Ando, Kaori ^{[1
]}

Hattori, Junichiro ^{[1
]}

机构：

[1] Gifu Univ, Fac Engn, Dept Chem & Biomol Sci, Yanagido 1-1, Gifu 5011193, Japan

来源：

TETRAHEDRON LETTERS | 2019年 / 60卷 / 36期

关键词：

Julia-Kocienski reagents; One-pot reaction; Sulfides from alcohols; Sulfones from alcohols; ALKYL ARYL SULFIDES; CONDENSATION; OLEFINATION; OXIDATION; ALDEHYDES; CATALYSTS;

D O I：

10.1016/j.tetlet.2019.151017

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A method for one-pot preparation of Julia-Kocienski sulfides and sulfones from alcohols and thiols is reported. A variety of primary alcohols were converted to the corresponding mesylates by methansulfonyl chloride and triethylamine in THF. After the reaction is complete, thiol (1 or 10) and either NaH or t-BuOK were added. The Julia-Kocienski sulfides 3, 9 and 11 were prepared by one-pot two steps procedure from alcohols in 76-96% yields (16 examples). Furthermore, after the sulfide formation, the reaction mixture was neutralized by p-toluenesulfonic acid and treated with H2O2 and ammonium molybdate in EtOH to give the Julia-Kocienski sulfones 4 in good yields except for trans-2-hexen-1-ol. (C) 2019 Elsevier Ltd. All rights reserved.

引用

页数：5

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