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配体对钯催化乙烯基酯二芳基化反应的影响

The Influence of Ligands on the Pd-Catalyzed Diarylation of Vinyl Esters.

作者信息

Brodzka Anna, Koszelewski Dominik, Trzeciak Anna, Ruzik Lena, Grela Malgorzata, Ostaszewski Ryszard

机构信息

Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland.

Faculty of Chemistry, University of Wrocław, F. Joliot-Curie 14, 50-383 Wrocław, Poland.

出版信息

Molecules. 2024 May 11;29(10):2268. doi: 10.3390/molecules29102268.

DOI:10.3390/molecules29102268
PMID:38792129
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11123883/
Abstract

The impact of ligands on the palladium-catalyzed 1,2-diarylation reaction course is presented. The application of Pd-dmpzc as a catalyst provides an efficient, chemoselective and sustainable protocol for the synthesis of valuable 1,2-diphenylethyl acetates. The reaction is conducted in water under mild conditions. Reaction products can be easily separated from the reaction mixture and catalyst by simple extraction. What is more, the rational choice of catalyst significantly reduces the leaching of the metal into the product and its contamination (0.1 ppm). Efficient phase separation and ultralow Pd leaching enable the reuse of the water medium containing the Pd-dmpzc catalyst several times without a significant loss of activity and with even higher selectivity (from 95% to 100% in the third cycle). The recyclability of both the catalyst and the reaction medium together with high chemoselectivity and low palladium leaching reduces the amount of waste and the cost of the process, exhibiting an example of a sustainable and green methodology.

摘要

本文介绍了配体对钯催化的1,2-二芳基化反应过程的影响。应用Pd-dmpzc作为催化剂为合成有价值的1,2-二苯基乙酸乙酯提供了一种高效、化学选择性和可持续的方法。该反应在温和条件下于水中进行。反应产物可通过简单萃取轻松地从反应混合物和催化剂中分离出来。此外,催化剂的合理选择显著减少了金属向产物中的浸出及其污染(0.1 ppm)。高效的相分离和超低的钯浸出使得含有Pd-dmpzc催化剂的水介质能够重复使用多次,而不会显著损失活性,甚至具有更高的选择性(在第三个循环中从95%提高到100%)。催化剂和反应介质的可循环利用性以及高化学选择性和低钯浸出减少了废物量和工艺成本,展示了一种可持续和绿色方法的实例。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f903/11123883/487b54334b7f/molecules-29-02268-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f903/11123883/ed9d7b67f0ac/molecules-29-02268-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f903/11123883/008a372c30c8/molecules-29-02268-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f903/11123883/6030c74c59f0/molecules-29-02268-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f903/11123883/406b4237422e/molecules-29-02268-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f903/11123883/487b54334b7f/molecules-29-02268-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f903/11123883/ed9d7b67f0ac/molecules-29-02268-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f903/11123883/008a372c30c8/molecules-29-02268-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f903/11123883/6030c74c59f0/molecules-29-02268-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f903/11123883/406b4237422e/molecules-29-02268-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f903/11123883/487b54334b7f/molecules-29-02268-sch002.jpg

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