Manganese-Catalyzed Synthesis of Polyketones Using Hydrogen-Borrowing Approach

IF 11.3 1区化学 Q1 CHEMISTRY, PHYSICAL

ACS Catalysis Pub Date : 2024-06-28 DOI:10.1021/acscatal.4c03019

Pavel S. Kulyabin, Oxana V. Magdysyuk, Aaron B. Naden, Daniel M. Dawson, Ketan Pancholi, Matthew Walker, Massimo Vassalli and Amit Kumar*,

引用次数: 0

Abstract

We report here a method of making polyketones from the coupling of diketones and diols using a manganese pincer complex. The methodology allows us to access various polyketones (polyarylalkylketone) containing aryl, alkyl, and ether functionalities, bridging the gap between the two classes of commercially available polyketones: aliphatic polyketones and polyaryletherketones. Using this methodology, 12 polyketones have been synthesized and characterized using various analytical techniques to understand their chemical, physical, morphological, and mechanical properties. Based on previous reports and our studies, we suggest that the polymerization occurs via a hydrogen-borrowing mechanism that involves the dehydrogenation of diols to dialdehyde followed by aldol condensation of dialdehyde with diketones to form chalcone derivatives and their subsequent hydrogenation to form polyarylalkylketones.

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利用借氢法锰催化合成聚酮化合物

我们在此报告一种利用锰钳复合物将二酮和二元醇偶联生成聚酮的方法。通过这种方法，我们可以获得含有芳基、烷基和醚官能团的各种聚酮（聚芳基烷基酮），从而弥补了脂肪族聚酮和聚芳醚酮这两类市售聚酮之间的差距。利用这种方法，我们合成了 12 种多酮类化合物，并使用各种分析技术对其进行了表征，以了解它们的化学、物理、形态和机械性能。根据以前的报告和我们的研究，我们认为聚合反应是通过借氢机制进行的，包括二元醇脱氢生成二醛，然后二醛与二酮发生醛醇缩合反应生成查尔酮衍生物，随后二酮发生氢化反应生成多芳基烷基酮。

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来源期刊

ACS Catalysis CHEMISTRY, PHYSICAL-

CiteScore

20.80

自引率

6.20%

发文量

1253

审稿时长

1.5 months

期刊介绍： ACS Catalysis is an esteemed journal that publishes original research in the fields of heterogeneous catalysis, molecular catalysis, and biocatalysis. It offers broad coverage across diverse areas such as life sciences, organometallics and synthesis, photochemistry and electrochemistry, drug discovery and synthesis, materials science, environmental protection, polymer discovery and synthesis, and energy and fuels. The scope of the journal is to showcase innovative work in various aspects of catalysis. This includes new reactions and novel synthetic approaches utilizing known catalysts, the discovery or modification of new catalysts, elucidation of catalytic mechanisms through cutting-edge investigations, practical enhancements of existing processes, as well as conceptual advances in the field. Contributions to ACS Catalysis can encompass both experimental and theoretical research focused on catalytic molecules, macromolecules, and materials that exhibit catalytic turnover.