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Synthesis, immobilization and catalytic activity of a copper(II) complex with a chiral bis(oxazoline)

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Synthesis, immobilization and catalytic activity of a copper(II) complex with a chiral bis(oxazoline). / Carneiro, Liliana; Silva, Ana R.; Shuttleworth, Peter S.; Budarin, Vitaly; Clark, James H.

In: MOLECULES, Vol. 19, No. 8, 08.2014, p. 11988-11998.

Research output: Contribution to journalArticle

Harvard

Carneiro, L, Silva, AR, Shuttleworth, PS, Budarin, V & Clark, JH 2014, 'Synthesis, immobilization and catalytic activity of a copper(II) complex with a chiral bis(oxazoline)', MOLECULES, vol. 19, no. 8, pp. 11988-11998. https://doi.org/10.3390/molecules190811988

APA

Carneiro, L., Silva, A. R., Shuttleworth, P. S., Budarin, V., & Clark, J. H. (2014). Synthesis, immobilization and catalytic activity of a copper(II) complex with a chiral bis(oxazoline). MOLECULES, 19(8), 11988-11998. https://doi.org/10.3390/molecules190811988

Vancouver

Carneiro L, Silva AR, Shuttleworth PS, Budarin V, Clark JH. Synthesis, immobilization and catalytic activity of a copper(II) complex with a chiral bis(oxazoline). MOLECULES. 2014 Aug;19(8):11988-11998. https://doi.org/10.3390/molecules190811988

Author

Carneiro, Liliana ; Silva, Ana R. ; Shuttleworth, Peter S. ; Budarin, Vitaly ; Clark, James H. / Synthesis, immobilization and catalytic activity of a copper(II) complex with a chiral bis(oxazoline). In: MOLECULES. 2014 ; Vol. 19, No. 8. pp. 11988-11998.

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@article{eb8e908bf34a40d983eaf31b5e0c4ce1,
title = "Synthesis, immobilization and catalytic activity of a copper(II) complex with a chiral bis(oxazoline)",
abstract = "A chiral bis(oxazoline) bearing CH2OH groups was synthesized from a commercial bis(oxazoline) and characterized by 1H- and 13C-NMR, high resolution ESI-mass spectrometry and FTIR. The corresponding copper(II) complex was immobilized onto the surface of a mesoporous carbonaceous material (Starbon{\circledR} 700) in which the double bonds had been activated via conventional bromination. The materials were characterized by elemental analysis, ICP-OES, XPS, thermogravimetry and nitrogen adsorption at 77 K. The new copper(II) bis(oxazoline) was tested both in the homogeneous phase and once immobilized onto a carbonaceous support for the kinetic resolution of hydrobenzoin. Both were active, enantioselective and selective in the mono-benzoylation of hydrobenzoin, but better enantioselectivities were obtained in the homogeneous phase. The heterogeneous catalyst could be separated from the reaction media at the end of the reaction and reused in another catalytic cycle, but with loss of product yield and enantioselectivity.",
keywords = "Asymmetric catalysis, Bis(oxazoline), Copper(II), Heterogeneous catalysis, Homogeneous catalysis",
author = "Liliana Carneiro and Silva, {Ana R.} and Shuttleworth, {Peter S.} and Vitaly Budarin and Clark, {James H.}",
year = "2014",
month = "8",
doi = "10.3390/molecules190811988",
language = "English",
volume = "19",
pages = "11988--11998",
journal = "MOLECULES",
issn = "1420-3049",
publisher = "Multidisciplinary Digital Publishing Institute (MDPI)",
number = "8",

}

RIS (suitable for import to EndNote) - Download

TY - JOUR

T1 - Synthesis, immobilization and catalytic activity of a copper(II) complex with a chiral bis(oxazoline)

AU - Carneiro, Liliana

AU - Silva, Ana R.

AU - Shuttleworth, Peter S.

AU - Budarin, Vitaly

AU - Clark, James H.

PY - 2014/8

Y1 - 2014/8

N2 - A chiral bis(oxazoline) bearing CH2OH groups was synthesized from a commercial bis(oxazoline) and characterized by 1H- and 13C-NMR, high resolution ESI-mass spectrometry and FTIR. The corresponding copper(II) complex was immobilized onto the surface of a mesoporous carbonaceous material (Starbon® 700) in which the double bonds had been activated via conventional bromination. The materials were characterized by elemental analysis, ICP-OES, XPS, thermogravimetry and nitrogen adsorption at 77 K. The new copper(II) bis(oxazoline) was tested both in the homogeneous phase and once immobilized onto a carbonaceous support for the kinetic resolution of hydrobenzoin. Both were active, enantioselective and selective in the mono-benzoylation of hydrobenzoin, but better enantioselectivities were obtained in the homogeneous phase. The heterogeneous catalyst could be separated from the reaction media at the end of the reaction and reused in another catalytic cycle, but with loss of product yield and enantioselectivity.

AB - A chiral bis(oxazoline) bearing CH2OH groups was synthesized from a commercial bis(oxazoline) and characterized by 1H- and 13C-NMR, high resolution ESI-mass spectrometry and FTIR. The corresponding copper(II) complex was immobilized onto the surface of a mesoporous carbonaceous material (Starbon® 700) in which the double bonds had been activated via conventional bromination. The materials were characterized by elemental analysis, ICP-OES, XPS, thermogravimetry and nitrogen adsorption at 77 K. The new copper(II) bis(oxazoline) was tested both in the homogeneous phase and once immobilized onto a carbonaceous support for the kinetic resolution of hydrobenzoin. Both were active, enantioselective and selective in the mono-benzoylation of hydrobenzoin, but better enantioselectivities were obtained in the homogeneous phase. The heterogeneous catalyst could be separated from the reaction media at the end of the reaction and reused in another catalytic cycle, but with loss of product yield and enantioselectivity.

KW - Asymmetric catalysis

KW - Bis(oxazoline)

KW - Copper(II)

KW - Heterogeneous catalysis

KW - Homogeneous catalysis

UR - http://www.scopus.com/inward/record.url?scp=84906691554&partnerID=8YFLogxK

U2 - 10.3390/molecules190811988

DO - 10.3390/molecules190811988

M3 - Article

VL - 19

SP - 11988

EP - 11998

JO - MOLECULES

JF - MOLECULES

SN - 1420-3049

IS - 8

ER -