<i>ortho</i>‐C−H Arylation of Benzoic Acids with Aryl Bromides and Chlorides Catalyzed by Ruthenium

Agostino Biafora, Thilo Krause, Dagmar Hackenberger, Florian Belitz, Lukas J. Gooßen

doi:10.1002/anie.201607270

<i>ortho</i>‐C−H Arylation of Benzoic Acids with Aryl Bromides and Chlorides Catalyzed by Ruthenium

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Agostino Biafora

FB Chemie-Organische Chemie TU Kaiserslautern Erwin-Schrödinger-Strasse Geb. 54 67663 Kaiserslautern Germany
Thilo Krause

Fakultät Chemie und Biochemie Ruhr Universität Bochum Universitätsstrasse 150 44801 Bochum Germany
Dagmar Hackenberger

Fakultät Chemie und Biochemie Ruhr Universität Bochum Universitätsstrasse 150 44801 Bochum Germany
Florian Belitz

FB Chemie-Organische Chemie TU Kaiserslautern Erwin-Schrödinger-Strasse Geb. 54 67663 Kaiserslautern Germany
Lukas J. Gooßen

Fakultät Chemie und Biochemie Ruhr Universität Bochum Universitätsstrasse 150 44801 Bochum Germany

書誌事項

公開日: 2016-10-21

権利情報

http://onlinelibrary.wiley.com/termsAndConditions#vor

DOI

10.1002/anie.201607270

公開者: Wiley

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説明

<jats:title>Abstract</jats:title><jats:p>A system consisting of catalytic amounts of [(<jats:italic>p</jats:italic>‐cym)RuCl<jats:sub>2</jats:sub>]<jats:sub>2</jats:sub>/PEt<jats:sub>3</jats:sub>⋅HBF<jats:sub>4</jats:sub>, K<jats:sub>2</jats:sub>CO<jats:sub>3</jats:sub> as the base, and NMP as the solvent efficiently mediates the <jats:italic>ortho</jats:italic>‐C−H arylation of benzoic acids with aryl bromides at 100 °C. Replacing the phosphine ligand with the amino acid <jats:sc>dl</jats:sc>‐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 <jats:italic>ipso</jats:italic> substitutions.</jats:p>