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对醌甲基化物与异腈的无金属氨羰基化反应:位阻α-芳基乙酰胺的合成

Metal-Free Aminocarbonylation of p-Quinone Methides with Isocyanides: Synthesis of Sterically Hindered α-Arylated Acetamides.

作者信息

Shirsath Sachin R, More Devidas A, Muthukrishnan M

机构信息

Division of Organic Chemistry, CSIR-National Chemical Laboratory, Pune, 411 008, India.

Academy of Scientific and Innovative Research (AcSIR), Ghaziabad, 201002, India.

出版信息

Chem Asian J. 2022 Oct 17;17(20):e202200642. doi: 10.1002/asia.202200642. Epub 2022 Sep 8.

Abstract

The synthesis of sterically hindered α-arylated acetamides generally requires a multistep reaction sequence and is also difficult to access due to steric constraints. This protocol allows the synthesis of sterically hindered α-arylated acetamides in moderate to high yields via 1,6-addition of isocyanides to p-quinone methides in the presence of BF .OEt . The present transformation features transition metal-free conditions, avoiding the use of toxic carbon monoxide, broad substrate scope, mild reaction conditions, and operational simplicity.

摘要

空间位阻α-芳基乙酰胺的合成通常需要多步反应序列,并且由于空间限制也难以实现。该方案允许在BF·OEt存在下,通过异腈对对苯醌甲基化物的1,6-加成,以中等至高收率合成空间位阻α-芳基乙酰胺。本转化具有无过渡金属条件,避免使用有毒的一氧化碳,底物范围广,反应条件温和以及操作简便等特点。

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