Preparation of acyl(carboxylato)bis(tertiary phosphine)palladium(II) complexes by C-O bond cleavage of carboxylic anhydrides on interaction with palladium(0) complexes. Catalytic hydrogenation of carboxylic anhydrides to aldehydes by palladium complexes

Kazuhiro Nagayama, Futoshi Kawataka, Masato Sakamoto, Isao Shimizu, Akio Yamamoto

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Abstract

Acyclic anhydrides oxidatively added to [Pd(styrene)(PMeR2)2] (R = Me, 2a; Ph, 2b) under mild conditions with C-O bond cleavage to give the corresponding trans-acyl(carboxylato)palladium complexes 3a-3h. Cyclic acid arthydrides also added to 2a to yield trans-acyl(carboxylato)palladium complexes 4a-4c, while reaction of 2a with phthalic anhydride afforded the palladalactone 4d generated via oxidative addition followed by decarbonylation. The acetyl(acetato)palladium complex 3a reacted with dihydrogen or formic acid to give acetaldehyde and acetic acid. Catalytic hydrogenation of acyclic anhydrides by a palladium complex was achieved to form the corresponding aldehydes and carboxylic acids.

Original languageEnglish
Pages (from-to)573-580
Number of pages8
JournalBulletin of the Chemical Society of Japan
Volume72
Issue number3
Publication statusPublished - 1999 Mar

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phosphine
Anhydrides
Palladium
Aldehydes
Hydrogenation
formic acid
Styrene
Acetaldehyde
Carboxylic Acids
Acetic Acid
Acids

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

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title = "Preparation of acyl(carboxylato)bis(tertiary phosphine)palladium(II) complexes by C-O bond cleavage of carboxylic anhydrides on interaction with palladium(0) complexes. Catalytic hydrogenation of carboxylic anhydrides to aldehydes by palladium complexes",
abstract = "Acyclic anhydrides oxidatively added to [Pd(styrene)(PMeR2)2] (R = Me, 2a; Ph, 2b) under mild conditions with C-O bond cleavage to give the corresponding trans-acyl(carboxylato)palladium complexes 3a-3h. Cyclic acid arthydrides also added to 2a to yield trans-acyl(carboxylato)palladium complexes 4a-4c, while reaction of 2a with phthalic anhydride afforded the palladalactone 4d generated via oxidative addition followed by decarbonylation. The acetyl(acetato)palladium complex 3a reacted with dihydrogen or formic acid to give acetaldehyde and acetic acid. Catalytic hydrogenation of acyclic anhydrides by a palladium complex was achieved to form the corresponding aldehydes and carboxylic acids.",
author = "Kazuhiro Nagayama and Futoshi Kawataka and Masato Sakamoto and Isao Shimizu and Akio Yamamoto",
year = "1999",
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volume = "72",
pages = "573--580",
journal = "Bulletin of the Chemical Society of Japan",
issn = "0009-2673",
publisher = "Chemical Society of Japan",
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TY - JOUR

T1 - Preparation of acyl(carboxylato)bis(tertiary phosphine)palladium(II) complexes by C-O bond cleavage of carboxylic anhydrides on interaction with palladium(0) complexes. Catalytic hydrogenation of carboxylic anhydrides to aldehydes by palladium complexes

AU - Nagayama, Kazuhiro

AU - Kawataka, Futoshi

AU - Sakamoto, Masato

AU - Shimizu, Isao

AU - Yamamoto, Akio

PY - 1999/3

Y1 - 1999/3

N2 - Acyclic anhydrides oxidatively added to [Pd(styrene)(PMeR2)2] (R = Me, 2a; Ph, 2b) under mild conditions with C-O bond cleavage to give the corresponding trans-acyl(carboxylato)palladium complexes 3a-3h. Cyclic acid arthydrides also added to 2a to yield trans-acyl(carboxylato)palladium complexes 4a-4c, while reaction of 2a with phthalic anhydride afforded the palladalactone 4d generated via oxidative addition followed by decarbonylation. The acetyl(acetato)palladium complex 3a reacted with dihydrogen or formic acid to give acetaldehyde and acetic acid. Catalytic hydrogenation of acyclic anhydrides by a palladium complex was achieved to form the corresponding aldehydes and carboxylic acids.

AB - Acyclic anhydrides oxidatively added to [Pd(styrene)(PMeR2)2] (R = Me, 2a; Ph, 2b) under mild conditions with C-O bond cleavage to give the corresponding trans-acyl(carboxylato)palladium complexes 3a-3h. Cyclic acid arthydrides also added to 2a to yield trans-acyl(carboxylato)palladium complexes 4a-4c, while reaction of 2a with phthalic anhydride afforded the palladalactone 4d generated via oxidative addition followed by decarbonylation. The acetyl(acetato)palladium complex 3a reacted with dihydrogen or formic acid to give acetaldehyde and acetic acid. Catalytic hydrogenation of acyclic anhydrides by a palladium complex was achieved to form the corresponding aldehydes and carboxylic acids.

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M3 - Article

VL - 72

SP - 573

EP - 580

JO - Bulletin of the Chemical Society of Japan

JF - Bulletin of the Chemical Society of Japan

SN - 0009-2673

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