Regioselective Synthesis of n‐Nonanal and Aldehyde‐Containing Polysiloxanes via Rh‐Catalyzed Hydroformylation Enhanced by A New Silicon‐Tethered Multidentate Phosphine Ligand

IF 2.5 3区 化学 Q2 CHEMISTRY, ORGANIC
Shu‐Yuan Tian , Lin Shi , Jun‐Hui Zhu , Dr. Li Li , Dr. Fei Ye , Prof. Dr. Zheng Xu , Prof. Dr. Li‐Wen Xu
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引用次数: 0

Abstract

Catalytic synthesis of long‐chain alkyl aldehydes presents a significant challenge in homogeneous catalysis and organic synthesis due to the difficulty in regioselective control. Here we report a rhodium‐catalyzed high chemo‐ and regio‐selective hydroformylation of 1‐octene that would be highly useful intermediates in chemical industry. Notably, the easy made tetradentate P‐ligands L1 and L2 can effectively suppress hydrogenation and isomerization reaction of olefins and give the desired aldehydes in high yield and good regioselectivity. Control experiments reveal the tetradentate P‐ligands is important for controlling selectivity because the high regioselectivity is found to benefit from the presence of four phosphorus atoms manifesting in the formation of much more efficient coordination interactions to give relatively stable rhodium complexes.

Abstract Image

一种新型硅系多齿膦配体增强的Rh催化氢甲酰化合成正壬醛和含醛聚硅氧烷的区域选择性
长链烷基醛的催化合成在均相催化和有机合成中都面临着巨大的挑战,因为它难以进行区域选择控制。在这里,我们报道了铑催化的高化学选择性和区域选择性的1 -辛烯氢甲酰化反应,这将是化学工业中非常有用的中间体。值得注意的是,易于制备的四齿P -配体L1和L2可以有效抑制烯烃的加氢和异构化反应,并以高收率和良好的区域选择性生成所需的醛。对照实验表明,四齿P配体对控制选择性很重要,因为发现高区域选择性得益于四个磷原子的存在,这表现在形成更有效的配位相互作用,从而产生相对稳定的铑配合物。
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来源期刊
CiteScore
5.40
自引率
3.60%
发文量
752
审稿时长
1 months
期刊介绍: The European Journal of Organic Chemistry (2019 ISI Impact Factor 2.889) publishes Full Papers, Communications, and Minireviews from the entire spectrum of synthetic organic, bioorganic and physical-organic chemistry. It is published on behalf of Chemistry Europe, an association of 16 European chemical societies. The following journals have been merged to form two leading journals, the European Journal of Organic Chemistry and the European Journal of Inorganic Chemistry: Liebigs Annalen Bulletin des Sociétés Chimiques Belges Bulletin de la Société Chimique de France Gazzetta Chimica Italiana Recueil des Travaux Chimiques des Pays-Bas Anales de Química Chimika Chronika Revista Portuguesa de Química ACH—Models in Chemistry Polish Journal of Chemistry.
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