A hydrogenative oxidation strategy for the single-step synthesis of lactams from N-heteroarenes using water

IF 42.8 1区 化学 Q1 CHEMISTRY, PHYSICAL Nature Catalysis Pub Date : 2025-01-20 DOI:10.1038/s41929-024-01286-2
Yaoyu Liang, Jie Luo, Cai You, Yael Diskin-Posner, David Milstein
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Abstract

Using water as a hydrogen or oxygen source in organic synthesis has enabled various reductive and oxidative transformations, but incorporation of both hydrogen and oxygen atoms into the same molecule, representing an atom-economic and environmentally benign process, has scarcely been explored. Here we report a hydrogenative oxidation strategy using water as both a source of H2 and formal oxidant, enabling the direct synthesis of lactams from N-heteroarenes and thereby eliminating the need for additional reductants and oxidants and minimizing waste generation. The reaction can be initiated either under low H2 pressure or with a catalytic amount of H2, leading to the efficient transformation of various N-heteroarenes into lactams in excellent yield thanks to an in situ-generated, piperidine-based, ruthenium pincer complex that balances the hydrogenation and dehydrogenation processes. This study will promote the design of other hydrogenative oxidation reactions using water.

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水催化n -杂芳烃一步合成内酰胺的氢化氧化策略
在有机合成中使用水作为氢或氧源已经实现了各种还原和氧化转化,但是将氢原子和氧原子结合到同一个分子中,这是一种原子经济和环境友好的过程,很少被探索。在这里,我们报道了一种氢化氧化策略,利用水作为H2和形式氧化剂的来源,使n -杂芳烃直接合成内酰胺,从而消除了对额外还原剂和氧化剂的需要,并最大限度地减少了废物的产生。该反应既可以在低H2压力下启动,也可以在催化量的H2下启动,由于现场生成的基于哌替啶的钌螯合物平衡了加氢和脱氢过程,导致各种n -杂芳烃高效转化为内酰胺,收率很高。该研究将促进其他用水加氢氧化反应的设计。
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来源期刊
Nature Catalysis
Nature Catalysis Chemical Engineering-Bioengineering
CiteScore
52.10
自引率
1.10%
发文量
140
期刊介绍: Nature Catalysis serves as a platform for researchers across chemistry and related fields, focusing on homogeneous catalysis, heterogeneous catalysis, and biocatalysts, encompassing both fundamental and applied studies. With a particular emphasis on advancing sustainable industries and processes, the journal provides comprehensive coverage of catalysis research, appealing to scientists, engineers, and researchers in academia and industry. Maintaining the high standards of the Nature brand, Nature Catalysis boasts a dedicated team of professional editors, rigorous peer-review processes, and swift publication times, ensuring editorial independence and quality. The journal publishes work spanning heterogeneous catalysis, homogeneous catalysis, and biocatalysis, covering areas such as catalytic synthesis, mechanisms, characterization, computational studies, nanoparticle catalysis, electrocatalysis, photocatalysis, environmental catalysis, asymmetric catalysis, and various forms of organocatalysis.
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