Relay catalysis over Pd-catalysts induced by two divergent ligands for cascade bis-alkoxycarbonylation of alkynes

IF 6.5 1区化学 Q2 CHEMISTRY, PHYSICAL Journal of Catalysis Pub Date : 2024-05-10 DOI:10.1016/j.jcat.2024.115543

Guang-Hui Shi , Yu-Fen Xie , Xiao-Xin Zhang , Jian-Guo Qian , Xiao-Li Zhao , Yong Lu , Hai-Jing Wang , Ye Liu

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Abstract

The mono-metal relay catalysis is a good strategy for one-pot multi-step cascade process in which the specific catalysis can be switched upon the ligand exchange to match the requirements for each independent reaction but without mutual interference and quenching problem. Herein, the one-pot cascade bis-alkoxycarbonylation of terminal alkynes was achieved by taking advantages of the mono-metallic (Pd) relay catalysis, wherein the two kinds of divergent di-phosphines of L1 and DTBPMB were involved. In this Pd(OAc)₂-L1-DTBPMB system, due to the steric bulkiness of L1 and DTBPMB, the two type of catalysts including Pd(OAc)₂-L1 and Pd(OAc)₂-DTBPMB co-existed independently and compatibly. Pd(OAc)₂-L1 system was only in charge of the first-step carbonylation of alkynes towards the branched α,β-unsaturated esters with gem-positioned double bond. Subsequent, Pd(OAc)₂-DTBPMB system took over the carbonylation of the branched α,β-unsaturated esters to afford the target diesters. It was indicated Pd(OAc)₂-L1 system was an efficient and stable catalyst which could be recycled upon 15 runs for the first-step carbonylation. Anyway, Pd(OAc)₂-DTBPMB system easily underwent deactivation, which degraded the recyclability of the Pd(OAc)₂-L1-DTBPMB coupling system for this cascade bis-alkoxycarbonylation.

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两种不同配体诱导的钯催化剂在炔烃的级联双-烷氧基羰基化过程中的中继催化作用

单金属中继催化是一种用于一锅多步级联反应的良好策略，它可以在配体交换时切换特定的催化反应，以满足每个独立反应的要求，但不会产生相互干扰和淬灭问题。本文利用单金属（钯）接力催化的优势，在 L1 和 DTBPMB 两种不同二膦的参与下，实现了端炔类化合物的一锅串联双烷氧基羰基化反应。在该 Pd(OAc)2-L1-DTBPMB 体系中，由于 L1 和 DTBPMB 的立体丰满度，Pd(OAc)2-L1 和 Pd(OAc)2-DTBPMB 两种催化剂可独立并存。Pd(OAc)2-L1 系统只负责炔烃的第一步羰基化，生成具有宝石位置双键的支链 α、β-不饱和酯。随后，Pd(OAc)2-DTBPMB 系统接管了支化 α、β- 不饱和酯的羰基化反应，从而得到目标二酯。结果表明，Pd(OAc)2-L1 系统是一种高效稳定的催化剂，可在第一步羰基化反应中循环使用 15 次。然而，Pd(OAc)2-DTBPMB 系统很容易失活，这降低了 Pd(OAc)2-L1-DTBPMB 偶联系统在该级联双烷氧羰基化反应中的可回收性。

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来源期刊

Journal of Catalysis 工程技术-工程：化工

CiteScore

12.30

自引率

5.50%

发文量

447

审稿时长

31 days

期刊介绍： The Journal of Catalysis publishes scholarly articles on both heterogeneous and homogeneous catalysis, covering a wide range of chemical transformations. These include various types of catalysis, such as those mediated by photons, plasmons, and electrons. The focus of the studies is to understand the relationship between catalytic function and the underlying chemical properties of surfaces and metal complexes. The articles in the journal offer innovative concepts and explore the synthesis and kinetics of inorganic solids and homogeneous complexes. Furthermore, they discuss spectroscopic techniques for characterizing catalysts, investigate the interaction of probes and reacting species with catalysts, and employ theoretical methods. The research presented in the journal should have direct relevance to the field of catalytic processes, addressing either fundamental aspects or applications of catalysis.