ortho-C-H Arylation of Benzoic Acids with Aryl Bromides and Chlorides Catalyzed by Ruthenium

被引：97

作者：

Biafora, Agostino ^{[1
]}

Krause, Thilo ^{[2
]}

Hackenberger, Dagmar ^{[2
]}

Belitz, Florian ^{[1
]}

Goossen, Lukas J. ^{[2
]}

机构：

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

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

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2016年 / 55卷 / 47期

关键词：

aryl halides; benzoic acids; biaryls; C-H arylation; ruthenium; CROSS-COUPLING REACTIONS; BIARYL COMPOUNDS; DIRECTING GROUPS; BOND ACTIVATION; FUNCTIONALIZATIONS; ALKENYLATION; CARBOXYLATES; STRATEGY;

D O I：

10.1002/anie.201607270

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A system consisting of catalytic amounts of [(p-cym)RuCl2](2)/PEt3 center dot HBF4, K2CO3 as the base, and NMP as the solvent efficiently mediates the ortho-C-H arylation of benzoic acids with aryl bromides at 100 degrees C. Replacing the phosphine ligand with the amino acid dl-pipecolinic acid enables the analogous transformation with aryl chlorides. The key advantage of this broadly applicable transformation is the use of an inexpensive ruthenium catalyst in combination with simple carboxylates as directing groups, which can either be tracelessly removed or used as anchor points for decarboxylative ipso substitutions.

引用

页码：14752 / 14755

页数：4

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