Chemoselective formation of cyclo-aliphatic and cyclo-olefinic 1,3-diols via pressure hydrogenation of potentially biobased platform molecules using Knölker-type catalysts

Christian A. M. R. van Slagmaat; Teresa Faber; Khi Chhay Chou; Alfonso J. Schwalb Freire; Darya Hadavi; Peiliang Han; Peter J. L. M. Quaedflieg; Gerard K. M. Verzijl; Paul L. Alsters; Stefaan M. A. De Wildeman

doi:10.1039/d1dt01252e

Chemoselective formation of cyclo-aliphatic and cyclo-olefinic 1,3-diols via pressure hydrogenation of potentially biobased platform molecules using Knölker-type catalysts

Christian A. M. R. van Slagmaat^*
, Teresa Faber
, Khi Chhay Chou
, Alfonso J. Schwalb Freire
, Darya Hadavi
, Peiliang Han
, Peter J. L. M. Quaedflieg
, Gerard K. M. Verzijl
, Paul L. Alsters
, Stefaan M. A. De Wildeman^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › Academic › peer-review

Abstract

The hydrogenative conversions of the biobased platform molecules 4-hydroxycyclopent-2-enone and cyclopentane-1,3-dione to their corresponding 1,3-diols are established using a pre-activated Knolker-type iron catalyst. The catalyst exhibits a high selectivity for ketone reduction, and does not induce dehydration. Moreover, by using different substituents of the ligand, the cis-trans ratio of the products can be affected substantially. A decent compatibility of this catalytic system with various structurally related substrates is demonstrated.

Original language	English
Pages (from-to)	10102-10112
Number of pages	11
Journal	Dalton Transactions
Volume	50
Issue number	29
DOIs	https://doi.org/10.1039/d1dt01252e
Publication status	Published - 7 Aug 2021

Keywords

IRON CATALYST
CONFORMATIONAL-ANALYSIS
COMPLEXES SYNTHESIS
BIOMASS
REDUCTION
TRANSFORMATION
CONVERSION
EFFICIENT
MECHANISM
KETONES

Access to Document

10.1039/d1dt01252e

Cite this

van Slagmaat, C. A. M. R., Faber, T., Chou, K. C., Freire, A. J. S., Hadavi, D., Han, P., Quaedflieg, P. J. L. M., Verzijl, G. K. M., Alsters, P. L., & De Wildeman, S. M. A. (2021). Chemoselective formation of cyclo-aliphatic and cyclo-olefinic 1,3-diols via pressure hydrogenation of potentially biobased platform molecules using Knölker-type catalysts. Dalton Transactions, 50(29), 10102-10112. https://doi.org/10.1039/d1dt01252e

@article{4c49e462d9e94c0cad17adf542ca5528,

title = "Chemoselective formation of cyclo-aliphatic and cyclo-olefinic 1,3-diols via pressure hydrogenation of potentially biobased platform molecules using Kn{\"o}lker-type catalysts",

abstract = "The hydrogenative conversions of the biobased platform molecules 4-hydroxycyclopent-2-enone and cyclopentane-1,3-dione to their corresponding 1,3-diols are established using a pre-activated Knolker-type iron catalyst. The catalyst exhibits a high selectivity for ketone reduction, and does not induce dehydration. Moreover, by using different substituents of the ligand, the cis-trans ratio of the products can be affected substantially. A decent compatibility of this catalytic system with various structurally related substrates is demonstrated.",

keywords = "IRON CATALYST, CONFORMATIONAL-ANALYSIS, COMPLEXES SYNTHESIS, BIOMASS, REDUCTION, TRANSFORMATION, CONVERSION, EFFICIENT, MECHANISM, KETONES",

author = "\{van Slagmaat\}, \{Christian A. M. R.\} and Teresa Faber and Chou, \{Khi Chhay\} and Freire, \{Alfonso J. Schwalb\} and Darya Hadavi and Peiliang Han and Quaedflieg, \{Peter J. L. M.\} and Verzijl, \{Gerard K. M.\} and Alsters, \{Paul L.\} and \{De Wildeman\}, \{Stefaan M. A.\}",

note = "Funding Information: This work was performed within the framework of the public-private knowledge institute of Chemelot InSciTe and is funded by contributions from the European Regional Development Fund (ERDF) within the framework of OP-Zuid and with contributions from the Dutch provinces of Noord-Brabant and Limburg and the Dutch Ministry of Economy. We gratefully acknowledge these agencies for their financial support. We also would like to thank Prof. Maarten Honing for offering his mass spectrometry equipment for our use. Publisher Copyright: {\textcopyright} The Royal Society of Chemistry 2021.",

year = "2021",

month = aug,

day = "7",

doi = "10.1039/d1dt01252e",

language = "English",

volume = "50",

pages = "10102--10112",

journal = "Dalton Transactions",

issn = "1477-9226",

publisher = "Royal Society of Chemistry",

number = "29",

}

van Slagmaat, CAMR, Faber, T, Chou, KC, Freire, AJS, Hadavi, D, Han, P, Quaedflieg, PJLM, Verzijl, GKM, Alsters, PL & De Wildeman, SMA 2021, 'Chemoselective formation of cyclo-aliphatic and cyclo-olefinic 1,3-diols via pressure hydrogenation of potentially biobased platform molecules using Knölker-type catalysts', Dalton Transactions, vol. 50, no. 29, pp. 10102-10112. https://doi.org/10.1039/d1dt01252e

Chemoselective formation of cyclo-aliphatic and cyclo-olefinic 1,3-diols via pressure hydrogenation of potentially biobased platform molecules using Knölker-type catalysts. / van Slagmaat, Christian A. M. R.; Faber, Teresa; Chou, Khi Chhay et al.
In: Dalton Transactions, Vol. 50, No. 29, 07.08.2021, p. 10102-10112.

Research output: Contribution to journal › Article › Academic › peer-review

TY - JOUR

T1 - Chemoselective formation of cyclo-aliphatic and cyclo-olefinic 1,3-diols via pressure hydrogenation of potentially biobased platform molecules using Knölker-type catalysts

AU - van Slagmaat, Christian A. M. R.

AU - Faber, Teresa

AU - Chou, Khi Chhay

AU - Freire, Alfonso J. Schwalb

AU - Hadavi, Darya

AU - Han, Peiliang

AU - Quaedflieg, Peter J. L. M.

AU - Verzijl, Gerard K. M.

AU - Alsters, Paul L.

AU - De Wildeman, Stefaan M. A.

N1 - Funding Information: This work was performed within the framework of the public-private knowledge institute of Chemelot InSciTe and is funded by contributions from the European Regional Development Fund (ERDF) within the framework of OP-Zuid and with contributions from the Dutch provinces of Noord-Brabant and Limburg and the Dutch Ministry of Economy. We gratefully acknowledge these agencies for their financial support. We also would like to thank Prof. Maarten Honing for offering his mass spectrometry equipment for our use. Publisher Copyright: © The Royal Society of Chemistry 2021.

PY - 2021/8/7

Y1 - 2021/8/7

N2 - The hydrogenative conversions of the biobased platform molecules 4-hydroxycyclopent-2-enone and cyclopentane-1,3-dione to their corresponding 1,3-diols are established using a pre-activated Knolker-type iron catalyst. The catalyst exhibits a high selectivity for ketone reduction, and does not induce dehydration. Moreover, by using different substituents of the ligand, the cis-trans ratio of the products can be affected substantially. A decent compatibility of this catalytic system with various structurally related substrates is demonstrated.

AB - The hydrogenative conversions of the biobased platform molecules 4-hydroxycyclopent-2-enone and cyclopentane-1,3-dione to their corresponding 1,3-diols are established using a pre-activated Knolker-type iron catalyst. The catalyst exhibits a high selectivity for ketone reduction, and does not induce dehydration. Moreover, by using different substituents of the ligand, the cis-trans ratio of the products can be affected substantially. A decent compatibility of this catalytic system with various structurally related substrates is demonstrated.

KW - IRON CATALYST

KW - CONFORMATIONAL-ANALYSIS

KW - COMPLEXES SYNTHESIS

KW - BIOMASS

KW - REDUCTION

KW - TRANSFORMATION

KW - CONVERSION

KW - EFFICIENT

KW - MECHANISM

KW - KETONES

U2 - 10.1039/d1dt01252e

DO - 10.1039/d1dt01252e

M3 - Article

C2 - 34240727

SN - 1477-9226

VL - 50

SP - 10102

EP - 10112

JO - Dalton Transactions

JF - Dalton Transactions

IS - 29

ER -

Chemoselective formation of cyclo-aliphatic and cyclo-olefinic 1,3-diols via pressure hydrogenation of potentially biobased platform molecules using Knölker-type catalysts

Abstract

Keywords

Access to Document

Fingerprint

Cite this