Directed C-H Bond Oxidation of Bridged Cycloalkanes Catalyzed by Palladium(II) Acetate.
Directed C-H Bond Oxidation of Bridged Cycloalkanes Catalyzed by Palladium(II) Acetate.
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DOI：
10.1002/chem.201800550
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发表时间：
2018-04
期刊：
影响因子：
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通讯作者：
Marta Larrosa;Benjamin Zonker;Jannis Volkmann;Felix Wech;C. Logemann;H. Hausmann;R. Hrdina
中科院分区：
文献类型：
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作者：
Marta Larrosa;Benjamin Zonker;Jannis Volkmann;Felix Wech;C. Logemann;H. Hausmann;R. Hrdina
我们发展了一种用乙酸钯催化的C-H键氧化合成1，2-取代金刚烷羧酸和进一步桥连的环烷烃（笼状化合物）的方法。使用吡啶甲酰胺作为导向基团进行环烷烃骨架的乙酰氧基化。通过对底物的修饰、配体的设计以及反应条件的改变，我们可以对脂肪族化合物的乙酰氧基化反应机理进行研究。开发了后官能化反应和定向基团的裂解。首次实现了β-C3 -三取代金刚烷衍生物的合成与表征。
We have developed a synthesis of 1,2-substituted adamantane carboxylic acids and further bridged cycloalkanes (cage compounds) by palladium acetate-catalyzed C-H bond oxidation. Acetoxylation of cycloalkane framework was performed using picolylamide as a directing group. Modification of the substrate, ligand design and variation of reaction conditions enabled us to study the mechanism of acetoxylation of aliphatic compounds. Post-functionalization reactions and cleavage of the directing group were developed. For the first time the synthesis and characterization of a β-C3 -tri-substituted adamantane derivatives was achieved.