New Sustainable Pd(II)/Fe(III) Catalytic System Very Efficient in the Hydromethoxycarbonylation of 1-octene

IF 16.4 1区化学 Q1 CHEMISTRY, MULTIDISCIPLINARY

Accounts of Chemical Research Pub Date : 2024-02-28 DOI:10.3311/ppch.22887

A. Vavasori, Beatrice Fantinel, L. Ronchin, Francesco Zanrosso, M. Bulybayev, N.J. Kudaibergenov, K. Shalmagambetov, G.J. Zhaksylykova

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Abstract

In order to increase the catalytic activity of the Pd(II)-complexes in the alcoxycarbonylation of 1-olefins, the presence in solution of a strong Brönsted acid together with a phosphine ligand is usually required. From an industrial point of view, such two additives, however, influenced the sustainability of the process mainly caused by the related corrosion of the reaction vessel and the toxicity of the phosphine ligand.In this paper, the methoxycarbonylation of 1-octene has been efficiently carried out by using the [Pd(TsO)2(PPh3)2]/FeCl3 catalyst system. The catalyst is very active also without addition of PPh3, reaching the TON of ca. 1300 (mol/mol) in 2 hours by using the Fe(III)/Pd(II) = 400/1 (mol/mol) system. Such value is higher than the values obtained by using the traditional strong Brönsted acid TsOH or other Lewis acid such as AlCl3, in the presence of PPh3. The reaction takes place with the formation of two isomeric products of linear and branched structures with a yield towards the linear isomer of ca. 80%.

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新型可持续钯(II)/铁(III)催化体系在 1-辛烯的氢甲氧基羰基化反应中非常高效

为了提高钯（II）络合物在 1-烯烃烷氧基羰基化反应中的催化活性，通常需要在溶液中加入强勃氏酸和膦配体。然而，从工业角度来看，这两种添加剂影响了工艺的可持续性，主要原因是反应容器的相关腐蚀和膦配体的毒性。本文使用 [Pd(TsO)2(PPh3)2]/FeCl3 催化剂体系有效地进行了 1-辛烯的甲氧基羰基化反应。该催化剂在不添加 PPh3 的情况下也非常活跃，在使用 Fe(III)/Pd(II) = 400/1 (mol/mol) 体系的情况下，2 小时内达到约 1300 (mol/mol) 的吨当量。这一数值高于在 PPh3 存在下使用传统的强勃氏酸 TsOH 或其他路易斯酸（如 AlCl3）所得到的数值。反应生成了线性和支化结构的两种异构产物，线性异构产物的产率约为 80%。

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来源期刊

Accounts of Chemical Research 化学-化学综合

CiteScore

31.40

自引率

1.10%

发文量

312

审稿时长

2 months

期刊介绍： Accounts of Chemical Research presents short, concise and critical articles offering easy-to-read overviews of basic research and applications in all areas of chemistry and biochemistry. These short reviews focus on research from the author’s own laboratory and are designed to teach the reader about a research project. In addition, Accounts of Chemical Research publishes commentaries that give an informed opinion on a current research problem. Special Issues online are devoted to a single topic of unusual activity and significance. Accounts of Chemical Research replaces the traditional article abstract with an article "Conspectus." These entries synopsize the research affording the reader a closer look at the content and significance of an article. Through this provision of a more detailed description of the article contents, the Conspectus enhances the article's discoverability by search engines and the exposure for the research.