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苯甲酸的区域特异性邻位碳氢键烯丙基化反应

Regiospecific ortho-C-H Allylation of Benzoic Acids.

作者信息

Trita A Stefania, Biafora Agostino, Pichette Drapeau Martin, Weber Philip, Gooßen Lukas J

机构信息

Fakultät Chemie und Biochemie, Ruhr Universität Bochum, Universitätsstr. 150, 44801, Bochum, Germany.

FB Chemie-Organische Chemie, TU Kaiserslautern, Erwin-Schrödinger-Str. Geb. 54, 67663, Kaiserslautern, Germany.

出版信息

Angew Chem Int Ed Engl. 2018 Oct 26;57(44):14580-14584. doi: 10.1002/anie.201712520. Epub 2018 Mar 5.

DOI:10.1002/anie.201712520
PMID:29411933
Abstract

A carboxylate-directed ortho-C-H functionalization has been developed and it allows the regiospecific introduction of allyl residues to benzoic acids. In the presence of a [Ru(p-cymene)Cl ] and K PO , benzoic acids react with allyl acetates at only 50 °C to give the corresponding ortho-allylbenzoic acids. The protocol is generally applicable to both electron-rich and electron-poor benzoic acids in combination with linear and branched allyl acetates. The products can be further functionalized in situ, for example, by double-bond migration, lactonization, or decarboxylation.

摘要

一种羧酸盐导向的邻位C-H官能团化反应已被开发出来,它能够将烯丙基残基区域特异性地引入苯甲酸中。在[Ru(p-异丙苯)Cl₂]和K₃PO₄存在下,苯甲酸仅在50°C时就能与醋酸烯丙酯反应,生成相应的邻烯丙基苯甲酸。该方案通常适用于富电子和缺电子的苯甲酸,以及线性和支链醋酸烯丙酯。产物可以进一步原位官能团化,例如通过双键迁移、内酯化或脱羧反应。

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