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DOI | 10.1126/science.abg2362 |
A tautomeric ligand enables directed C‒H hydroxylation with molecular oxygen | |
Zhen Li; Zhen Wang; Nikita Chekshin; Shaoqun Qian; Jennifer X. Qiao; Peter T. Cheng; Kap-Sun Yeung; William R. Ewing; Jin-Quan Yu | |
2021-06-25 | |
发表期刊 | Science |
出版年 | 2021 |
英文摘要 | Although oxygen is all around us, it is often surprisingly difficult to use it for selective chemical oxidations, necessitating more expensive, wasteful alternatives. Li et al. report that careful ligand optimization produces palladium catalysts that can efficiently activate oxygen to hydroxylate a variety of aryl and heteroaromatic rings adjacent to a carboxylic acid substituent. The ligand binds to palladium through pyridine and pyridone components, and the authors posit that tautomerization between dative and anionic coordination modes plays a role in its effectiveness. Science , abg2362, this issue p. [1452][1] Hydroxylation of aryl carbon–hydrogen bonds with transition metal catalysts has proven challenging when oxygen is used as the oxidant. Here, we report a palladium complex bearing a bidentate pyridine/pyridone ligand that efficiently catalyzes this reaction at ring positions adjacent to carboxylic acids. Infrared, x-ray, and computational analysis support a possible role of ligand tautomerization from mono-anionic (L,X) to neutral (L,L) coordination in the catalytic cycle of aerobic carbon–hydrogen hydroxylation reaction. The conventional site selectivity dictated by heterocycles is overturned by this catalyst, thus allowing late-stage modification of compounds of pharmaceutical interest at previously inaccessible sites. [1]: /lookup/doi/10.1126/science.abg2362 |
领域 | 气候变化 ; 资源环境 |
URL | 查看原文 |
引用统计 | |
文献类型 | 期刊论文 |
条目标识符 | http://119.78.100.173/C666/handle/2XK7JSWQ/334147 |
专题 | 气候变化 资源环境科学 |
推荐引用方式 GB/T 7714 | Zhen Li,Zhen Wang,Nikita Chekshin,等. A tautomeric ligand enables directed C‒H hydroxylation with molecular oxygen[J]. Science,2021. |
APA | Zhen Li.,Zhen Wang.,Nikita Chekshin.,Shaoqun Qian.,Jennifer X. Qiao.,...&Jin-Quan Yu.(2021).A tautomeric ligand enables directed C‒H hydroxylation with molecular oxygen.Science. |
MLA | Zhen Li,et al."A tautomeric ligand enables directed C‒H hydroxylation with molecular oxygen".Science (2021). |
条目包含的文件 | 条目无相关文件。 |
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