Heterogeneous asymmetric reactions: Part 38. Enantioselective hydrogenation of fluoroketones on Pt-alumina catalyst

Research output: Contribution to journalArticle

46 Citations (Scopus)

Abstract

The enantioselective heterogeneous hydrogenation of 2,2,2- trifluoroacetophenone (1), 4-(trifluoroacetyl)biphenyl (5) and other fluoroketones (2-4, 6-8) on modified (by cinchonidine) Pt-alumina (E4759) in toluene solution with and without trifluoroacetic acid (TFA) has been investigated. The effects of the modifier concentration (0-10 mmol/l), hydrogen pressure (1-50 bar), temperature (263-301 K) and conversion on the reaction rate and the enantioselectivity (ee) were studied. The achieved ee was 85% in case of 1, however 67% ee was achieved in case of 5. It has been proposed that the compounds responsible for chiral induction are the intermediate complexes, the structure of which depends on whether hydrogenation is performed with or without TFA.

Original languageEnglish
Pages (from-to)181-187
Number of pages7
JournalJournal of Molecular Catalysis A: Chemical
Volume216
Issue number2
DOIs
Publication statusPublished - Jul 12 2004

Fingerprint

Aluminum Oxide
Enantioselectivity
Hydrogenation
hydrogenation
Trifluoroacetic acid
Trifluoroacetic Acid
Alumina
aluminum oxides
catalysts
acids
Catalysts
toluene
induction
reaction kinetics
Toluene
Reaction rates
Hydrogen
hydrogen
temperature
Temperature

Keywords

  • Cinchonidine
  • Enantioselective
  • Fluoroketones
  • Hydrogenation
  • Intermediate complexes
  • Platinum-alumina

ASJC Scopus subject areas

  • Catalysis
  • Process Chemistry and Technology

Cite this

@article{ac4b78dd77ee4399a28cb344c7265dca,
title = "Heterogeneous asymmetric reactions: Part 38. Enantioselective hydrogenation of fluoroketones on Pt-alumina catalyst",
abstract = "The enantioselective heterogeneous hydrogenation of 2,2,2- trifluoroacetophenone (1), 4-(trifluoroacetyl)biphenyl (5) and other fluoroketones (2-4, 6-8) on modified (by cinchonidine) Pt-alumina (E4759) in toluene solution with and without trifluoroacetic acid (TFA) has been investigated. The effects of the modifier concentration (0-10 mmol/l), hydrogen pressure (1-50 bar), temperature (263-301 K) and conversion on the reaction rate and the enantioselectivity (ee) were studied. The achieved ee was 85{\%} in case of 1, however 67{\%} ee was achieved in case of 5. It has been proposed that the compounds responsible for chiral induction are the intermediate complexes, the structure of which depends on whether hydrogenation is performed with or without TFA.",
keywords = "Cinchonidine, Enantioselective, Fluoroketones, Hydrogenation, Intermediate complexes, Platinum-alumina",
author = "Tibor Varga and K. Felf{\"o}ldi and P. Forg{\'o} and M. Bart{\'o}k",
year = "2004",
month = "7",
day = "12",
doi = "10.1016/j.molcata.2004.03.019",
language = "English",
volume = "216",
pages = "181--187",
journal = "Journal of Molecular Catalysis A: Chemical",
issn = "1381-1169",
publisher = "Elsevier",
number = "2",

}

TY - JOUR

T1 - Heterogeneous asymmetric reactions

T2 - Part 38. Enantioselective hydrogenation of fluoroketones on Pt-alumina catalyst

AU - Varga, Tibor

AU - Felföldi, K.

AU - Forgó, P.

AU - Bartók, M.

PY - 2004/7/12

Y1 - 2004/7/12

N2 - The enantioselective heterogeneous hydrogenation of 2,2,2- trifluoroacetophenone (1), 4-(trifluoroacetyl)biphenyl (5) and other fluoroketones (2-4, 6-8) on modified (by cinchonidine) Pt-alumina (E4759) in toluene solution with and without trifluoroacetic acid (TFA) has been investigated. The effects of the modifier concentration (0-10 mmol/l), hydrogen pressure (1-50 bar), temperature (263-301 K) and conversion on the reaction rate and the enantioselectivity (ee) were studied. The achieved ee was 85% in case of 1, however 67% ee was achieved in case of 5. It has been proposed that the compounds responsible for chiral induction are the intermediate complexes, the structure of which depends on whether hydrogenation is performed with or without TFA.

AB - The enantioselective heterogeneous hydrogenation of 2,2,2- trifluoroacetophenone (1), 4-(trifluoroacetyl)biphenyl (5) and other fluoroketones (2-4, 6-8) on modified (by cinchonidine) Pt-alumina (E4759) in toluene solution with and without trifluoroacetic acid (TFA) has been investigated. The effects of the modifier concentration (0-10 mmol/l), hydrogen pressure (1-50 bar), temperature (263-301 K) and conversion on the reaction rate and the enantioselectivity (ee) were studied. The achieved ee was 85% in case of 1, however 67% ee was achieved in case of 5. It has been proposed that the compounds responsible for chiral induction are the intermediate complexes, the structure of which depends on whether hydrogenation is performed with or without TFA.

KW - Cinchonidine

KW - Enantioselective

KW - Fluoroketones

KW - Hydrogenation

KW - Intermediate complexes

KW - Platinum-alumina

UR - http://www.scopus.com/inward/record.url?scp=2542456591&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=2542456591&partnerID=8YFLogxK

U2 - 10.1016/j.molcata.2004.03.019

DO - 10.1016/j.molcata.2004.03.019

M3 - Article

AN - SCOPUS:2542456591

VL - 216

SP - 181

EP - 187

JO - Journal of Molecular Catalysis A: Chemical

JF - Journal of Molecular Catalysis A: Chemical

SN - 1381-1169

IS - 2

ER -