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
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
收藏
页码:10364 / 10369
页数:6
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