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室温下溶剂控制的酰氯酰胺化反应：通往适用于后期官能化的芳香族伯酰胺和酰亚胺的新途径。

Solvent-controlled amidation of acid chlorides at room temperature: new route to access aromatic primary amides and imides amenable for late-stage functionalization.

作者信息

Sivaraj Chandrasekaran, Gandhi Thirumanavelan

机构信息

Department of Chemistry, School of Advanced Sciences, Vellore Institute of Technology Vellore 632014 Tamil Nadu India

出版信息

RSC Adv. 2023 Mar 21;13(14):9231-9236. doi: 10.1039/d3ra00403a. eCollection 2023 Mar 20.

DOI:10.1039/d3ra00403a
PMID:36959886
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC10028618/
Abstract

Herein, we report a solvent-controlled highly selective amidation and imidation of aroyl chlorides using an alkali-metal silyl-amide reagent (LiHMDS), which serves as a nitrogen source at room temperature. A unique feature of this method lies in the sequential silyl amidation of aryol chlorides and nitrogen-silicon bond cleavage of the corresponding ,-bis(trimethylsilyl)benzamide in a one-pot method in a very short reaction time. This effective strategy was extended to late-stage functionalization.

摘要

在此，我们报道了一种在室温下使用碱金属硅烷基酰胺试剂（LiHMDS）作为氮源，通过溶剂控制实现芳酰氯的高选择性酰胺化和亚胺化反应。该方法的独特之处在于，在非常短的反应时间内，通过一锅法依次实现芳酰氯的硅烷基酰胺化以及相应的α，α-双（三甲基硅基）苯甲酰胺的氮-硅键断裂。这种有效策略已扩展至后期官能团化反应。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c3f6/10028618/9b2d077e0558/d3ra00403a-s7.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c3f6/10028618/5a0e70a00112/d3ra00403a-s1.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c3f6/10028618/8b671674d412/d3ra00403a-s5.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c3f6/10028618/9b2d077e0558/d3ra00403a-s7.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c3f6/10028618/5a0e70a00112/d3ra00403a-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c3f6/10028618/10b0f93a193c/d3ra00403a-s2.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c3f6/10028618/1e0692945043/d3ra00403a-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c3f6/10028618/8b671674d412/d3ra00403a-s5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c3f6/10028618/3b28d861d43d/d3ra00403a-s6.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c3f6/10028618/9b2d077e0558/d3ra00403a-s7.jpg

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