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固体酸作为烯烃和炔烃螯合辅助氢酰化反应中的共催化剂。

Solid acids as cocatalysts in the chelation-assisted hydroacylation of alkenes and alkynes.

作者信息

Vergara-Arenas Blanca I, García-Ríos Eréndira, Gaviño Rubén, Cárdenas Jorge, Martinez-Garcia Alfredo, Juarez-Arellano Erick A, López-Torres Adolfo, Morales-Serna José A

机构信息

Departamento de Química, Universidad Autónoma Metropolitana-Iztapalapa Av. San Rafael Atlixco No. 186 Ciudad de México C. P. 09340 Mexico.

Instituto de Química, Universidad Nacional Autónoma de México, Circuito Exterior, Ciudad Universitaria Ciudad de México 04510 Mexico

出版信息

RSC Adv. 2024 Oct 7;14(43):31675-31682. doi: 10.1039/d4ra05791k. eCollection 2024 Oct 1.

DOI:10.1039/d4ra05791k
PMID:39376529
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11457000/
Abstract

The use of homogeneous Brønsted acid cocatalysts (such as benzoic acid) in hydroacylation reactions imine intermediates has been extensively studied. However, the use of heterogeneous cocatalysts has been limited to montmorillonite K10. Thus, we can use other solid acids to increase the efficiency of the reaction. In this study, we describe the effects of sulfated zirconia, Al-MCM-41 or superacid modified montmorillonite on the hydroacylation of alkenes and alkynes with aldehydes imine intermediates and in the presence of the Wilkinson complex. Furthermore, we addressed the dual role of montmorillonite, a redox reagent in the presence of TEMPO and an acid solid, allowing the direct use of benzyl alcohols as substrates to generate saturated or α,β-unsaturated ketones.

摘要

在氢酰化反应中使用均相布朗斯特酸共催化剂（如苯甲酸）与亚胺中间体的情况已得到广泛研究。然而，非均相共催化剂的使用仅限于蒙脱石K10。因此，我们可以使用其他固体酸来提高反应效率。在本研究中，我们描述了硫酸化氧化锆、Al-MCM-41或超酸改性蒙脱石对烯烃和炔烃与醛在亚胺中间体存在下以及在威尔金森配合物存在下进行氢酰化反应的影响。此外，我们探讨了蒙脱石的双重作用，即在TEMPO存在下作为氧化还原试剂以及作为酸性固体，从而允许直接使用苄醇作为底物生成饱和或α,β-不饱和酮。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3964/11457000/33aa91ef4565/d4ra05791k-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3964/11457000/1e6ed9bd2cf3/d4ra05791k-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3964/11457000/9545dd8f7cd8/d4ra05791k-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3964/11457000/453df3582acf/d4ra05791k-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3964/11457000/c945c052a5e0/d4ra05791k-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3964/11457000/33aa91ef4565/d4ra05791k-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3964/11457000/1e6ed9bd2cf3/d4ra05791k-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3964/11457000/9545dd8f7cd8/d4ra05791k-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3964/11457000/453df3582acf/d4ra05791k-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3964/11457000/c945c052a5e0/d4ra05791k-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3964/11457000/33aa91ef4565/d4ra05791k-s2.jpg

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