Hydrogenation of trans-Cinnamaldehyde with Hydrido-Carbonyl Osmium(II) Complexes of Chelating Phosphine Ligands

Min Kyo Jung, Seong Huh, Wonyong Lee, Moo Jin Jun

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

A series of new hydridocarhonyl osmium(II) complexes, OsHCl(CO)(PPh3)(L-L)[L-L=Ph2P(CH2) nPPh2 (n=1 (1), 2 (2), 3 (3), cis-Ph2PCH=CHPPh2 (4), and Fe(η5-C5H4PPh2)2 (5)] has been synthesized from OsHCl(CO)(PPh3)3 and chelating diphosphines. These complexes have been characterized by IR. 1H NMR and elemental analysis. The catalytic activities of these complexes both for the transfer hydrogenation of trans-cinnamaldehyde with 2-propanol as the hydrogen donor, and for the selective hydrogenation of trans-cinnamaldehyde with H2, have been examined. Complexes (1)-(5) were shown to have higher selectivities for the transfer hydrogenation of the C=O bond of aldehyde than for the transfer hydrogenation of the C=C bond of aldehyde. The selectivities for the transfer hydrogenation with 2-propanol as well as for the hydrogenation with H2 have been found to decrease in the order 3>5>2>4>1. Complex (3) has shown to possess almost 90% of the selectivity to cinnamyl alcohol for transfer hydrogenation. It is also found that there is a correlation between the v(CO) of each complex and the hydrogenation, of the C=O bond of trans-cinnamaldehyde. Overall, the selectivities with the complexes (1)-(5) are greater for the transfer hydrogenation with 2-propanol than for the hydrogenation with H2.

Original languageEnglish
Pages (from-to)806-810
Number of pages5
JournalBulletin of the Korean Chemical Society
Volume18
Issue number8
Publication statusPublished - 1997 Dec 1

Fingerprint

phosphine
Osmium
Chelation
Hydrogenation
Ligands
2-Propanol
Aldehydes
cinnamic aldehyde

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

Cite this

@article{5cfd6d054370440f8afba47a5c951148,
title = "Hydrogenation of trans-Cinnamaldehyde with Hydrido-Carbonyl Osmium(II) Complexes of Chelating Phosphine Ligands",
abstract = "A series of new hydridocarhonyl osmium(II) complexes, OsHCl(CO)(PPh3)(L-L)[L-L=Ph2P(CH2) nPPh2 (n=1 (1), 2 (2), 3 (3), cis-Ph2PCH=CHPPh2 (4), and Fe(η5-C5H4PPh2)2 (5)] has been synthesized from OsHCl(CO)(PPh3)3 and chelating diphosphines. These complexes have been characterized by IR. 1H NMR and elemental analysis. The catalytic activities of these complexes both for the transfer hydrogenation of trans-cinnamaldehyde with 2-propanol as the hydrogen donor, and for the selective hydrogenation of trans-cinnamaldehyde with H2, have been examined. Complexes (1)-(5) were shown to have higher selectivities for the transfer hydrogenation of the C=O bond of aldehyde than for the transfer hydrogenation of the C=C bond of aldehyde. The selectivities for the transfer hydrogenation with 2-propanol as well as for the hydrogenation with H2 have been found to decrease in the order 3>5>2>4>1. Complex (3) has shown to possess almost 90{\%} of the selectivity to cinnamyl alcohol for transfer hydrogenation. It is also found that there is a correlation between the v(CO) of each complex and the hydrogenation, of the C=O bond of trans-cinnamaldehyde. Overall, the selectivities with the complexes (1)-(5) are greater for the transfer hydrogenation with 2-propanol than for the hydrogenation with H2.",
author = "Jung, {Min Kyo} and Seong Huh and Wonyong Lee and Jun, {Moo Jin}",
year = "1997",
month = "12",
day = "1",
language = "English",
volume = "18",
pages = "806--810",
journal = "Bulletin of the Korean Chemical Society",
issn = "0253-2964",
publisher = "Korean Chemical Society",
number = "8",

}

Hydrogenation of trans-Cinnamaldehyde with Hydrido-Carbonyl Osmium(II) Complexes of Chelating Phosphine Ligands. / Jung, Min Kyo; Huh, Seong; Lee, Wonyong; Jun, Moo Jin.

In: Bulletin of the Korean Chemical Society, Vol. 18, No. 8, 01.12.1997, p. 806-810.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Hydrogenation of trans-Cinnamaldehyde with Hydrido-Carbonyl Osmium(II) Complexes of Chelating Phosphine Ligands

AU - Jung, Min Kyo

AU - Huh, Seong

AU - Lee, Wonyong

AU - Jun, Moo Jin

PY - 1997/12/1

Y1 - 1997/12/1

N2 - A series of new hydridocarhonyl osmium(II) complexes, OsHCl(CO)(PPh3)(L-L)[L-L=Ph2P(CH2) nPPh2 (n=1 (1), 2 (2), 3 (3), cis-Ph2PCH=CHPPh2 (4), and Fe(η5-C5H4PPh2)2 (5)] has been synthesized from OsHCl(CO)(PPh3)3 and chelating diphosphines. These complexes have been characterized by IR. 1H NMR and elemental analysis. The catalytic activities of these complexes both for the transfer hydrogenation of trans-cinnamaldehyde with 2-propanol as the hydrogen donor, and for the selective hydrogenation of trans-cinnamaldehyde with H2, have been examined. Complexes (1)-(5) were shown to have higher selectivities for the transfer hydrogenation of the C=O bond of aldehyde than for the transfer hydrogenation of the C=C bond of aldehyde. The selectivities for the transfer hydrogenation with 2-propanol as well as for the hydrogenation with H2 have been found to decrease in the order 3>5>2>4>1. Complex (3) has shown to possess almost 90% of the selectivity to cinnamyl alcohol for transfer hydrogenation. It is also found that there is a correlation between the v(CO) of each complex and the hydrogenation, of the C=O bond of trans-cinnamaldehyde. Overall, the selectivities with the complexes (1)-(5) are greater for the transfer hydrogenation with 2-propanol than for the hydrogenation with H2.

AB - A series of new hydridocarhonyl osmium(II) complexes, OsHCl(CO)(PPh3)(L-L)[L-L=Ph2P(CH2) nPPh2 (n=1 (1), 2 (2), 3 (3), cis-Ph2PCH=CHPPh2 (4), and Fe(η5-C5H4PPh2)2 (5)] has been synthesized from OsHCl(CO)(PPh3)3 and chelating diphosphines. These complexes have been characterized by IR. 1H NMR and elemental analysis. The catalytic activities of these complexes both for the transfer hydrogenation of trans-cinnamaldehyde with 2-propanol as the hydrogen donor, and for the selective hydrogenation of trans-cinnamaldehyde with H2, have been examined. Complexes (1)-(5) were shown to have higher selectivities for the transfer hydrogenation of the C=O bond of aldehyde than for the transfer hydrogenation of the C=C bond of aldehyde. The selectivities for the transfer hydrogenation with 2-propanol as well as for the hydrogenation with H2 have been found to decrease in the order 3>5>2>4>1. Complex (3) has shown to possess almost 90% of the selectivity to cinnamyl alcohol for transfer hydrogenation. It is also found that there is a correlation between the v(CO) of each complex and the hydrogenation, of the C=O bond of trans-cinnamaldehyde. Overall, the selectivities with the complexes (1)-(5) are greater for the transfer hydrogenation with 2-propanol than for the hydrogenation with H2.

UR - http://www.scopus.com/inward/record.url?scp=0031326231&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0031326231&partnerID=8YFLogxK

M3 - Article

VL - 18

SP - 806

EP - 810

JO - Bulletin of the Korean Chemical Society

JF - Bulletin of the Korean Chemical Society

SN - 0253-2964

IS - 8

ER -