Direct hydrogenation of carboxylic acids to corresponding aldehydes catalyzed by palladium complexes

K. Nagayama, I. Shimizu, A. Yamamoto

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55 Citations (Scopus)

Abstract

A variety of carboxylic acids can be directly hydrogenated into the corresponding aldehydes in high yields by using homogeneous catalysts such as [Pd(PPh3)4] or combination of Pd(OAc)2 with tertiary phosphines in the presence of an excess amount of 2,2-dimethylpropionic anhydride (pivalic anhydride). As a typical example, octanoic acid can be convened into octanal in 99% yield in 3 h at 80 °C under 3.0 MPa of H2 in acetone in the presence of pivalic anhydride and a catalyst system composed of Pd(OAc)2 + 5P(p-tol)3. Such hydrogenation is widely applicable to various aliphatic, aromatic, and heterocyclic carboxylic acids as well as to di- and tribasic carboxylic acids. The process allows the presence of other functional groups such as ketonic carbonyl, nitrile, and ester groups and even internal C=C bonds. Heterogeneous palladium catalyst such as palladium on carbon also showed some catalytic activities.

Original languageEnglish
Pages (from-to)1803-1815
Number of pages13
JournalBulletin of the Chemical Society of Japan
Volume74
Issue number10
DOIs
Publication statusPublished - 2001 Oct

ASJC Scopus subject areas

  • Chemistry(all)

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