Regiospecific ortho-C-H Allylation of Benzoic Acids

被引：75

作者：

Trita, A. Stefania ^{[1
]}

Biafora, Agostino ^{[2
]}

Drapeau, Martin Pichette ^{[1
]}

Weber, Philip ^{[1
]}

Goossen, Lukas J. ^{[1
]}

机构：

[1] Ruhr Univ Bochum, Fak Chem & Biochem, Univ Str 150, D-44801 Bochum, Germany

[2] TU Kaiserslautern, FB Chem Organ Chem, Erwin Schrodinger Str Geb 54, D-67663 Kaiserslautern, Germany

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2018年 / 57卷 / 44期

关键词：

allylation; C-H activation; carboxylic acids; reaction mechanisms; ruthenium; TRACELESS DIRECTING GROUPS; ELECTRON-DEFICIENT ARENES; CARBOXYLIC-ACIDS; ORTHO-ARYLATION; ARYL; HYDROARYLATION; ACTIVATION; ACETATES; ALKYNES; BONDS;

D O I：

10.1002/anie.201712520

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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-2](2) and K3PO4, benzoic acids react with allyl acetates at only 50 degrees 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.

引用

页码：14580 / 14584

页数：5

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