三氟甲磺酸三甲基硅酯介导的吲哚的傅-克羟基烷基化反应

Friedel-Crafts Hydroxyalkylation of Indoles Mediated by Trimethylsilyl Trifluoromethanesulfonate.

作者信息

Downey C Wade, Poff Christopher D, Nizinski Alissa N

机构信息

University of Richmond , Gottwald Center for the Sciences, 28 Westhampton Way, Richmond, Virginia 23173, United States.

出版信息

J Org Chem. 2015 Oct 16;80(20):10364-9. doi: 10.1021/acs.joc.5b01681. Epub 2015 Sep 29.

DOI:10.1021/acs.joc.5b01681

PMID:26393376

Abstract

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.

摘要

在三甲基甲硅烷基三氟甲磺酸酯和三烷基胺存在下，吲哚和N - 烷基吲哚与醛发生傅克加成反应，生成3-(1-硅氧基烷基)吲哚。用吡啶中和反应混合物，然后在碱性条件下用四丁基氟化铵进行脱保护，得到作为游离醇的1:1加合物。该方法可防止所需产物自发转化为热力学上更有利的双吲哚基(芳基)甲烷，这是吲哚在酸性条件下与醛反应时通常会观察到的过程。