Mg(OtBu)2-catalyzed C–H oxidation of α-azido arylethanones using TBHP as the oxidant and carbonyl oxygen source: facile access to primary α-ketoamides

Peng, Yingying; Zhuo, Bi-Yin; Wang, Zhiqiang; Liu, Bang; Zhang, Fuxing; Yu, Jiangxi; Wang, Chengyong; Xu, Zhifeng; Li, Jin‐Heng

doi:10.1039/d2qo01226j

Org. Chem. Front.

2022

DOI: 10.1039/d2qo01226j

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Mg(O^tBu)₂-catalyzed C–H oxidation of α-azido arylethanones using TBHP as the oxidant and carbonyl oxygen source: facile access to primary α-ketoamides

Yingying Peng

Bi-Yin Zhuo

Zhiqiang Wang

et al.

Abstract: A room temperature Mg(OtBu)2-catalyzed C(sp3)-H oxidation of α-azido arylethanones to straightforwardly produce primary α-ketoamides is presented. By utilizing TBHP as the oxidant and carbonyl oxygen source, this method allows oxidation...

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2024

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Cited by 2 publications

References 41 publications

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De Novo Synthesis of α‐Ketoamides via Pd/TBD Synergistic Catalysis

Chen,

Zhang,

Wang

et al. 2024

Advanced Science

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Precisely controlling the product selectivity of a reaction is an important objective in organic synthesis. α‐Ketoamides are vital intermediates in chemical transformations and privileged motifs in numerous drugs, natural products, and biologically active molecules. The selective synthesis of α‐ketoamides from feedstock chemicals in a safe and operationally simple manner under mild conditions is a long‐standing catalysis challenge. Herein, an unprecedented TBD‐switched Pd‐catalyzed double isocyanide insertion reaction for assembling ketoamides in aqueous DMSO from (hetero)aryl halides and pseudohalides under mild conditions is reported. The effectiveness and utility of this protocol are demonstrated by its diverse substrate scope (93 examples), the ability to late‐stage modify pharmaceuticals, scalability to large‐scale synthesis, and the synthesis of pharmaceutically active molecules. Mechanistic studies indicate that TBD is a key ligand that modulates the Pd‐catalyzed double isocyanide insertion process, thereby selectively providing the desired α‐ketoamides in a unique manner. In addition, the imidoylpalladium(II) complex and α‐ketoimine amide are successfully isolated and determined by X‐ray analysis, confirming that they are probable intermediates in the catalytic pathway.

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De Novo Synthesis of α‐Ketoamides via Pd/TBD Synergistic Catalysis

Chen,

Zhang,

Wang

et al. 2024

Advanced Science

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Preparation of Phenacyl Azides and Their Application Advances in Organic Synthesis

She,

Wang,

Liu

et al. 2024

Chinese Journal of Organic Chemistry

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Phenacyl azides, a kind of crucial organic azide, serve as a valuable synthetic substrate in organic synthesis. They have extensive applications in constructing diverse nitrogen-containing compounds. Their straightforward synthetic methods, elevated reactivity and multiple reaction sites enable them to undergo reactions at a single site or simultaneously at multiple sites, resulting in a wide range of reaction types. Based on the significant progress made in organic synthesis in recent years, various preparation methods of phenacyl azides and research results classified according to specific reaction types are mainly reviewed. Representative examples and reaction mechanisms are discussed and analyzed. Keywords phenacyl azide; preparation; types of reaction; application advance 自 1864 年 Griess [1] 发现苯基叠氮化合物以来, 化学工作者们陆续发展了许多有机叠氮化合物转化的新方法、新反应, 使得该类化合物在有机合成中得到广泛的应用. 有机叠氮化合物作为一类非常重要的合成砌块, 常被用于构筑各种氮杂环化合物, 在医药 [2] 、染料 [3] 、生物 [4] 及材料 [5] 等领域都起到了不可或缺的作用 [6] .

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Mg(O^tBu)₂-catalyzed C–H oxidation of α-azido arylethanones using TBHP as the oxidant and carbonyl oxygen source: facile access to primary α-ketoamides

Abstract: A room temperature Mg(OtBu)2-catalyzed C(sp3)-H oxidation of α-azido arylethanones to straightforwardly produce primary α-ketoamides is presented. By utilizing TBHP as the oxidant and carbonyl oxygen source, this method allows oxidation...

Cited by 2 publications

References 41 publications

De Novo Synthesis of α‐Ketoamides via Pd/TBD Synergistic Catalysis

De Novo Synthesis of α‐Ketoamides via Pd/TBD Synergistic Catalysis

Preparation of Phenacyl Azides and Their Application Advances in Organic Synthesis

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