Friedel-Crafts Hydroxyalkylation of Indoles Mediated by Trimethylsilyi Trifluoromethanesulfonate

被引：24

作者：

Downey, C. Wade ^{[1
]}

Poff, Christopher D. ^{[1
]}

Nizinski, Alissa N. ^{[1
]}

机构：

[1] Univ Richmond, Gottwald Ctr Sci, Richmond, VA 23173 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2015年 / 80卷 / 20期

基金：

美国国家科学基金会;

关键词：

CARBONYL-COMPOUNDS;

D O I：

10.1021/acs.joc.5b01681

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Indoles and N-alkylindoles undergo Friedel Crafts addition to aldehydes in the presence of trimethylsilyl trifluoromethanesulfonate and a trialkylamine to produce 3-(1-silyloxyalkyl)-indoles. Neutralization of the reaction mixture with pyridine followed by deprotection under basic conditions with tetrabutylammonium fluoride provides the 1:1 adduct as the free alcohol. This method prevents spontaneous conversion of the desired products to the thermodynamically favored bisindolyl(aryl)methanes, a process typically observed when indoles are reacted with aldehydes under acidic conditions.

引用

页码：10364 / 10369

页数：6

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