Hydrogen-deuterium exchange of aromatic amines and amides using deuterated trifluoroacetic acid

被引：16
|
作者：
Giles, Richard
Lee, Amy
Jung, Erica
Kang, Aaron
Jung, Kyung Woon [1 ]
机构：
[1] Univ So Calif, Laker Hydrocarbon Res Inst, Los Angeles, CA 90089 USA
来源：
TETRAHEDRON LETTERS | 2015年 / 56卷 / 05期
关键词：
H-D exchange; CF3COOD; Acetaminophen; Electrophilic aromatic substitution; Bronsted acid; ACETAMINOPHEN; TRYPTOPHAN; KINETICS; ESTRONE; NMR;
D O I：
10.1016/j.tetlet.2014.12.102
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The H-D exchange of aromatic amines and amides, including pharmaceutically relevant compounds such as acetaminophen and diclofenac, was investigated using CF3COOD as both the sole reaction solvent and source of deuterium label. The described method is amenable to efficient deuterium incorporation for a wide variety of substrates possessing both electron-donating and electron-withdrawing substituents. Best results were seen with less basic anilines and highly activated acetanilides, reflecting the likelihood of different mechanistic pathways. (C) 2014 Elsevier Ltd. All rights reserved.
引用
收藏
页码：747 / 749
页数：3
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