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

K. Nagayama, I. Shimizu, A. Yamamoto

Research output: Contribution to journalArticle

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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

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Palladium
Carboxylic Acids
Aldehydes
Hydrogenation
Catalysts
Phosphines
Nitriles
Acetone
Functional groups
Catalyst activity
Esters
Carbon
palladium(II) acetate
pivalic anhydride

ASJC Scopus subject areas

  • Chemistry(all)

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Direct hydrogenation of carboxylic acids to corresponding aldehydes catalyzed by palladium complexes. / Nagayama, K.; Shimizu, I.; Yamamoto, A.

In: Bulletin of the Chemical Society of Japan, Vol. 74, No. 10, 10.2001, p. 1803-1815.

Research output: Contribution to journalArticle

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AB - 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.

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