HIGHLY EFFICIENT ONE-POT SYNTHESIS OF N-ALKYL SULFONAMIDES FROM ALCOHOLS USING N-(p-TOLUENESULFONYL) IMIDAZOLE (TSIM)

被引：1
|
作者：
Rad, Mohammad Navid Soltani [1 ]
Behrouz, Somayeh [1 ]
Nekoei, Abdo-Reza [1 ]
机构：
[1] Shiraz Univ Technol, Dept Chem, Shiraz 71555313, Iran
来源：
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS | 2014年 / 189卷 / 04期
关键词：
Alcohol; N-alkylation; potassium sulfonylamide salt; TsIm; triethylamine (TEA); DFT study; CATALYZED DIRECT AMINATION; INTERMOLECULAR HYDROAMINATION; DIRECT CONVERSION; BENZYL ALCOHOLS; AMINES; ACID; AMIDATION; INHIBITORS; MITSUNOBU; CHLORIDE;
D O I：
10.1080/10426507.2013.829828
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
A facile and efficient method for one-pot synthesis of N-alkyl sulfonamides from alcohols using N-(p-toluenesulfonyl)imidazole (TsIm) is described. In this protocol, treatment of various potassium sulfonylamide salts and alcohols in the presence of TsIm and triethylamine in refluxing DMF furnishes the corresponding N-alkyl sulfonamides in good to excellent yields. This methodology is highly efficient for reaction of various structurally diverse primary and secondary alcohols as well as potassium sulfonylamides. Also, the density functional theoretical calculations are employed to mechanistically study this protocol. [Supplementary materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements for the following free supplemental files: Additional text and figures.]
引用
收藏
页码：465 / 476
页数：12
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