Regiospecific ortho-C-H Allylation of Benzoic Acids

被引：76
|
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
收藏
页码：14580 / 14584
页数：5
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