Enabling Efficient Synthesis of Dihydrostilbenoid via Palladium-Catalyzed Redox-Neutral Deacylative Arylation

IF 11.3 1区化学 Q1 CHEMISTRY, PHYSICAL

ACS Catalysis Pub Date : 2025-05-27 DOI:10.1021/acscatal.5c02437

Yafei Wan, Tengfei Kang, Zhehui Xu, Weikang Xiong, Gang Li, Jianyang Dong, Dong Xue

引用次数: 0

Abstract

Carbon–Carbon (C–C) bonds constitute the fundamental framework of organic molecules, and their cleavage and reorganization play pivotal roles in both biological systems and industrial processes. Herein, we present a palladium-catalyzed deacylative arylation of diverse methyl ketones under light-free and redox-neutral conditions, offering an efficient approach to constructing C(sp²)–C(sp³) bonds. This radical cross-coupling protocol features a broad substrate scope and good functional group compatibility, facilitating the late-stage modification of drug molecules and the synthesis of bioactive natural dihydrostilbenoids. The process leverages a redox-neutral mechanism, wherein the palladium complex serves as an oxidant and the ketone-derived prearomatic intermediates (PAIs) act as a reductant. Mechanistic investigations validate our hypothesis regarding the dual roles of the palladium complex in this transformation.

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钯催化氧化还原中性脱酰芳基化高效合成二氢二苯乙烯

碳碳键（C-C）是有机分子的基本结构，其裂解和重组在生物系统和工业过程中都起着关键作用。在此，我们提出了钯催化的多种甲基酮在无光和氧化还原中性条件下的脱酰芳化反应，为构建C(sp2) -C （sp3）键提供了一种有效的方法。这种自由基交叉偶联方案具有底物范围广、官能团相容性好等特点，有利于药物分子的后期修饰和生物活性天然二氢二苯乙烯类化合物的合成。该工艺利用氧化还原-中性机制，其中钯配合物作为氧化剂，酮衍生的芳香前中间体（PAIs）作为还原剂。机理研究证实了我们关于钯配合物在这一转变中的双重作用的假设。

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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.