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杂芳基酯的多相铃木-宫浦偶联反应:化学选择性C(酰基)-O键活化

Heterogeneous Suzuki-Miyaura coupling of heteroaryl ester chemoselective C(acyl)-O bond activation.

作者信息

Ma Hongpeng, Bai Chaolumen, Bao Yong-Sheng

机构信息

College of Chemistry and Environmental Science, Inner Mongolia Key Laboratory of Green Catalysis, Inner Mongolia Normal University Hohhot 010022 China

出版信息

RSC Adv. 2019 Jun 3;9(30):17266-17272. doi: 10.1039/c9ra02394a. eCollection 2019 May 29.

DOI:10.1039/c9ra02394a
PMID:35519852
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9064562/
Abstract

A site-selective supported palladium nanoparticle catalyzed Suzuki-Miyaura cross-coupling reaction with heteroaryl esters and arylboronic acids as coupling partners was developed. This methodology provides a heterogeneous catalytic route for aryl ketone formation C(acyl)-O bond activation of esters by successful suppression of the undesired decarbonylation phenomenon. The catalyst can be reused and shows high activity after eight cycles. The XPS analysis of the catalyst before and after the reaction suggested that the reaction might be performed a Pd/Pd catalytic cycle that began with Pd.

摘要

开发了一种以杂芳基酯和芳基硼酸作为偶联伙伴的位点选择性负载钯纳米颗粒催化的铃木-宫浦交叉偶联反应。该方法通过成功抑制不期望的脱羰现象,为芳基酮的形成提供了一条非均相催化途径,实现了酯的C(酰基)-O键活化。该催化剂可重复使用,经过八个循环后仍显示出高活性。反应前后催化剂的XPS分析表明,反应可能是通过以Pd开始的Pd/Pd催化循环进行的。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cfb6/9064562/efe4c9cd2946/c9ra02394a-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cfb6/9064562/74ce05c1235e/c9ra02394a-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cfb6/9064562/f9cbf96f5a1d/c9ra02394a-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cfb6/9064562/3534c901e023/c9ra02394a-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cfb6/9064562/eb594c0a46a5/c9ra02394a-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cfb6/9064562/efe4c9cd2946/c9ra02394a-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cfb6/9064562/74ce05c1235e/c9ra02394a-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cfb6/9064562/f9cbf96f5a1d/c9ra02394a-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cfb6/9064562/3534c901e023/c9ra02394a-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cfb6/9064562/eb594c0a46a5/c9ra02394a-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cfb6/9064562/efe4c9cd2946/c9ra02394a-s2.jpg

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本文引用的文献

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RSC Adv. 2018 Jul 13;8(44):25168-25176. doi: 10.1039/c8ra04984j. eCollection 2018 Jul 9.
2
Ligand-Controlled Chemoselective C(acyl)-O Bond vs C(aryl)-C Bond Activation of Aromatic Esters in Nickel Catalyzed C(sp)-C(sp) Cross-Couplings.配体控制的选择性 C(酰基)-O 键与 C(芳基)-C 键断裂在镍催化 C(sp)-C(sp)交叉偶联反应中芳香酯的反应。
J Am Chem Soc. 2018 Mar 14;140(10):3724-3735. doi: 10.1021/jacs.7b12865. Epub 2018 Mar 2.
3
Selective Reductive Removal of Ester and Amide Groups from Arenes and Heteroarenes through Nickel-Catalyzed C-O and C-N Bond Activation.
通过镍催化的 C-O 和 C-N 键活化,从芳烃和杂芳烃中选择性还原去除酯基和酰胺基。
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Catalytic Ester and Amide to Amine Interconversion: Nickel-Catalyzed Decarbonylative Amination of Esters and Amides by C-O and C-C Bond Activation.催化酯和酰胺到胺的转化:通过 C-O 和 C-C 键活化的镍催化酯和酰胺的脱羰基氨化反应。
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