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碳酸丙烯酯作为铃木-宫浦反应中可持续溶剂的范围及局限性

Scope and limitation of propylene carbonate as a sustainable solvent in the Suzuki-Miyaura reaction.

作者信息

Czompa Andrea, Pásztor Balázs László, Sahar Jennifer Alizadeh, Mucsi Zoltán, Bogdán Dóra, Ludányi Krisztina, Varga Zoltán, Mándity István M

机构信息

Department of Organic Chemistry, Faculty of Pharmacy, Semmelweis University Hőgyes Endre u. 7 H-1092 Budapest Hungary

Femtonics Ltd Tűzoltó u. 59 H-1094 Budapest Hungary.

出版信息

RSC Adv. 2019 Nov 20;9(65):37818-37824. doi: 10.1039/c9ra07044c. eCollection 2019 Nov 19.

DOI:10.1039/c9ra07044c
PMID:35541805
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9075783/
Abstract

The Suzuki-Miyaura reaction is one of the most used transformations in drug research. Thus making this reaction more sustainable is of considerable current interest. Here we show that propylene carbonate (PC) can be used as a solvent for the Suzuki-Miyaura reaction. PC is one of the greenest solvents since it is synthesized under green conditions by the use of carbon dioxide in the air. All reactions proceeded well and good or excellent yields were observed for the biaryl products. Nonetheless in the case of pyridazinones, 2-hydroxypropyl- chain containing side-products were observed. Importantly, this fact allowed the isolation of several novel compounds which were generated under prominently green conditions.

摘要

铃木-宫浦反应是药物研究中最常用的转化反应之一。因此,提高该反应的可持续性在当前备受关注。在此我们表明碳酸丙烯酯(PC)可作为铃木-宫浦反应的溶剂。PC是最绿色的溶剂之一,因为它是在绿色条件下利用空气中的二氧化碳合成的。所有反应进行顺利,联芳基产物的产率良好或优异。然而,在哒嗪酮的情况下,观察到含有2-羟丙基链的副产物。重要的是,这一事实使得能够分离出在显著绿色条件下生成的几种新型化合物。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/afd0/9075783/321cbe84ec90/c9ra07044c-s9.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/afd0/9075783/580a055d649a/c9ra07044c-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/afd0/9075783/d6ae9f2ee44f/c9ra07044c-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/afd0/9075783/549ae61fed8f/c9ra07044c-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/afd0/9075783/6d9fa3025797/c9ra07044c-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/afd0/9075783/6fcd9119ff3d/c9ra07044c-s5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/afd0/9075783/6a44733031d8/c9ra07044c-s6.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/afd0/9075783/0b5bab0da2b6/c9ra07044c-s7.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/afd0/9075783/b4cf8f9f1c41/c9ra07044c-s8.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/afd0/9075783/f8d388b17a59/c9ra07044c-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/afd0/9075783/321cbe84ec90/c9ra07044c-s9.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/afd0/9075783/580a055d649a/c9ra07044c-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/afd0/9075783/d6ae9f2ee44f/c9ra07044c-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/afd0/9075783/549ae61fed8f/c9ra07044c-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/afd0/9075783/6d9fa3025797/c9ra07044c-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/afd0/9075783/6fcd9119ff3d/c9ra07044c-s5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/afd0/9075783/6a44733031d8/c9ra07044c-s6.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/afd0/9075783/0b5bab0da2b6/c9ra07044c-s7.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/afd0/9075783/b4cf8f9f1c41/c9ra07044c-s8.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/afd0/9075783/f8d388b17a59/c9ra07044c-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/afd0/9075783/321cbe84ec90/c9ra07044c-s9.jpg

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本文引用的文献

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Beilstein J Org Chem. 2020 May 13;16:1001-1005. doi: 10.3762/bjoc.16.89. eCollection 2020.
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