One-pot synthesis of 2-methylfurans from 3-(trimethylsilyl)propargyl acetates promoted by trimethylsilyl trifluoromethanesulfonate

被引：5
|
作者：
Sklar, Danielle E. [1 ]
Helbling, Alex, V [1 ]
Liu, Yiqi [1 ]
Downey, C. Wade [1 ]
机构：
[1] Univ Richmond, Gottwald Ctr Sci, 138 UR Dr, Richmond, VA 23173 USA
来源：
TETRAHEDRON LETTERS | 2021年 / 87卷
基金：
美国国家科学基金会;
关键词：
Furan synthesis; Silyl triflate; One-pot reactions; Cyclizations; RING-SYSTEMS FURANS; NUCLEOPHILIC-SUBSTITUTION; PROPARGYLIC ACETATES; INHIBITION; ESTERS; ENTRY;
D O I：
10.1016/j.tetlet.2021.153424
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
In the presence of trimethylsilyl trifluoromethanesulfonate (TMSOTf) and triethylamine, 3-(trimethylsilyl)propargyl carboxylates undergo a one-pot alkylation-cyclization-desilylation reaction with ketones to produce 2-methylfurans. Alkylation at 0 degrees C in methylene chloride, followed by acid-catalyzed cyclization at room temperature, provides the furans in 52-86% yield. Cyclization and desilylation appear to be promoted by triflic acid generated in situ from the exposure of the reaction mixture to water upon completion of the initial substitution reaction. (c) 2021 Elsevier Ltd. All rights reserved.
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页数：4
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