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Dehydrogenative Synthesis of Carboxylic Acids from Primary Alcohols and Hydroxide Catalyzed by a Ruthenium N-Heterocyclic Carbene Complex

Carola Santilli, Ilya S. Makarov, Peter Fristrup and Robert Madsen*

*Department of Chemistry, Technical University of Denmark, DK-2800 Lyngby, Denmark, Email: rmkemi.dtu.dk

C. Santilli, I. S. Makarov, P. Fristrup, R. Madsen, J. Org. Chem., 2016, 81, 9931-9938.

DOI: 10.1021/acs.joc.6b02105 (free Supporting Information)


Abstract

A dehydrogenative reaction of primary alcohols in the presence of hydroxide and the ruthenium complex [RuCl2(IPr)(p-cymene)] as catalyst provides carboxylic acids. The use of toluene enables a simple product isolation by precipitation and extraction. A range of benzylic and saturated aliphatic alcohols containing halide and (thio)ether substituents can be converted, while olefins and ester groups are not compatible.

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Key Words

carboxylic acids


ID: J42-Y2016