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通过钯催化芳烃 C-H 功能化合成酚类化合物。

Synthesis of Phenolic Compounds via Palladium Catalyzed C-H Functionalization of Arenes.

机构信息

Department of Chemistry, Krishnagar Govt. College, Krishnagar, Nadia, 741101, India.

School of Chemical Sciences, Indian Association for the Cultivation of Science, 2A & 2B Raja S. C. Mullick Road, Jadavpur, Kolkata, 700032, India.

出版信息

Chem Asian J. 2019 Dec 13;14(24):4534-4548. doi: 10.1002/asia.201901073. Epub 2019 Nov 28.

Abstract

Phenol and its derivatives are extremely useful compounds in organic synthesis, medicinal chemistry and material sciences. The synthesis of phenols involving selective construction of the C-O bond at a C-H bond of arenes using transition-metal catalysis represents the most appealing strategy. Indeed, active research is currently going on for the synthesis of valuable phenolic compounds using a transition-metal-catalyzed C-H functionalization strategy. This short review summarizes recent advances on palladium-catalyzed C-O bond forming reactions that enable direct access to phenolic compounds. These catalytic reactions proceed either via C-H esterification with trifluoroacetic acid/trifluoroacetic anhydride followed by in situ hydrolysis of the ester or via direct C-H hydroxylation. A brief analysis of substrate scope and limitation, reaction mechanism as well as synthetic utility of these reactions has been included.

摘要

苯酚及其衍生物在有机合成、药物化学和材料科学中是非常有用的化合物。使用过渡金属催化选择性地在芳环的 C-H 键上构建 C-O 键的苯酚合成代表了最吸引人的策略。事实上,目前正在积极研究使用过渡金属催化的 C-H 官能化策略合成有价值的酚类化合物。这篇简短的综述总结了最近在钯催化的 C-O 键形成反应方面的进展,这些反应可以直接得到酚类化合物。这些催化反应要么通过三氟乙酸/三氟乙酸酐与 C-H 的酯化反应进行,然后进行原位酯水解,要么通过直接 C-H 羟化反应进行。本文还简要分析了这些反应的底物范围和限制、反应机理以及它们的合成实用性。

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