Formal Decarbonylation of 1,2-Diketones Enabled by Synergistic Catalysis of Lewis Acid–Base Pairs and Redox Properties in CeO2

IF 11.3 1区化学 Q1 CHEMISTRY, PHYSICAL ACS Catalysis Pub Date : 2024-06-21 DOI:10.1021/acscatal.4c02493

Takehiro Matsuyama, Takafumi Yatabe* and Kazuya Yamaguchi*,

引用次数: 0

Abstract

Various decarbonylation reactions via oxidative addition of carbonyl compounds to metal catalysts can be applied to late-stage modification and have been actively studied to date; however, several inherent problems derived from the oxidative addition are difficult to solve, such as toxic CO production, deactivation of catalysts by CO adsorption, intolerance of some functional groups, or air-sensitivity of catalysts. In this context, formal decarbonylation, which eliminates CO as other compounds without involving oxidative addition, is attractive but hardly reported, especially using heterogeneous catalysts. Herein, formal decarbonylation of diaryl 1,2-diketones to afford monoketones using CeO₂ as a reusable heterogeneous catalyst and O₂ in the air as the terminal oxidant was developed, generating CO₂ as the only byproduct. The results revealed that the reaction was enabled by the synergistic catalytic effect of the Lewis acid–base pairs and redox properties in CeO₂.

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通过路易斯酸碱对的协同催化和 CeO2 中的氧化还原特性实现 1,2-二酮的正式脱羰基反应

通过将羰基化合物氧化加成到金属催化剂上的各种脱羰基反应可应用于后期改性，迄今为止，人们对这些反应进行了积极的研究；然而，氧化加成产生的一些固有问题难以解决，如有毒 CO 的产生、催化剂因吸附 CO 而失活、某些官能团的不耐受性或催化剂对空气的敏感性。在这种情况下，形式脱羰基反应（不涉及氧化加成就能像消除其他化合物一样消除 CO）很有吸引力，但鲜有报道，尤其是使用异质催化剂。本文以 CeO2 为可重复使用的异质催化剂，以空气中的 O2 为末端氧化剂，对 1,2-二酮类二芳基化合物进行了形式脱羰基反应，生成了单酮类化合物，唯一的副产物是 CO2。研究结果表明，CeO2 中路易斯酸碱对和氧化还原特性的协同催化作用使反应得以进行。

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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.