Kleij

Research group

FULL REPORT

Abstract

Our research activities currently focus on the valorization/upgrading of carbon dioxide and renewable feedstocks into value-added organic molecules using rational organocatalytic and metal-mediated catalytic approaches. In order to achieve these goals we use highly functional organic cyclic carbonates as versatile and accessible synthetic precursors. A primary focus is on sustainable solutions thereby improving on (1) overall activity and chemo-selectivity, and (2) stereo-chemical challenges. Our targeted portfolio of organic structures includes complex organic carbonates, allylic derivatives, amino acids and propargylic compounds through innovative stereo-selective or enantioselective coupling approaches. An important part of our work puts attention to new catalyst design and efforts to reach a higher level of mechanistic understanding concerning the observed reactivity/selectivity features through experimental and computational studies. Interdisciplinary collaborations with the industrial in the area of biobased polymers also form part of our activities in order to be able to transfer technological advancements from bench to and beyond pilot scale.

Topics addressed

Cyclic carbonates
Fine chemical synthesis
Bio-based polymers

Articles

“Pd-Catalyzed Enantio- and Regioselective Formation of Allylic Aryl Ethers “
Org. Lett. (2017) 19 – 6388-6391
J. Xie, W. Guo, A. Cai, E.C. Escudero-Adán, A.W. Kleij

“Copper-Mediated SN₂′ Allyl−Alkyl and Allyl−Boryl Couplings of Vinyl Cyclic Carbonates
Org. Lett. (2017) 19 – 6096-6099
N. Miralles, J.E. Gómez, A.W. Kleij, E. Fernández

“Polystyrene-supported bifunctional resorcinarenes as cheap, metal-free and recyclable catalysts for epoxide/CO₂ coupling reactions”
Green Chem. (2017) 19 – 5488-5493
T. Jose, S. Cañellas, M.A. Pericàs, A.W. Kleij

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“Copper-Catalyzed Synthesis of g-Amino Acids Featuring Quaternary Stereocenters”
Angew. Chem. Int. Ed. (2017) 56 – 15035-15038
J.E. Gómez, W. Guo, S. Gaspa, A.W. Kleij

“Asymmetric Synthesis of a,a-Disubstituted Allylic Amines via Pd-Catalyzed Allylic Substitution”
Angew. Chem. Int. Ed. (2017) 56 – 11797-11801
W. Guo, A. Cai, J. Xie, A.W. Kleij

“Semiaromatic Polyesters Derived from Renewable Terpene Oxides with High Glass Transitions”
Macromolecules (2017) 50 – 5337-5345
L. Peña-Carrodeguas, C. Martín, A.W. Kleij

“Substrate Triggered Stereoselective Preparation of Highly Substituted Organic Carbonates”
ACS Catal. (2017) 7 – 5478-5482
V. Laserna, E. Martin, E.C. Escudero-Adán, A.W. Kleij

“Fatty Acid Based Biocarbonates: Al-Mediated Stereoselective Preparation of Mono-, Di- and Tricarbonates under Mild and Solvent-less Conditions”
Green Chem. (2017) 19 – 3535-3541
L. Peña-Carrodeguas, A. Cristòfol, J.M. Fraile, J.A. Mayoral, V. Dorado-Horrillo, C.I. Herrerías, A.W. Kleij

“Access to Biorenewable Polycarbonates with Unusual Glass-Transition Temperature (T_g) Modulation”
ACS Catal. (2017) 7, 3860-3863
N. Kindermann, A. Cristòfol, A.W. Kleij

“Pushing the Limits with Squaramide-based Organocatalysts in Cyclic Carbonate Synthesis”
ACS Catal. (2017) 7 – 3532-3539
S. Sopeña, E. Martín, E.C. Escudero-Adán, A.W. Kleij

“Metal-Free Synthesis of N-Aryl Amides using Organocatalytic Ring-Opening Aminolysis of Lactones”
ChemSusChem (2017) 10 – 1969-1975
W. Guo, J. Enrique Gómez, L. Martínez-Rodríguez, N.A.G. Bandeira, C. Bo, A.W. Kleij

“CO₂ Catalysis – Editorial“
ChemSusChem (2017) 10 – 1036-1038
A.W. Kleij, M. North, A. Urakawa

“Vanadium(V) Catalysts with High Activity for the Coupling of Epoxides and CO₂: Characterization of a putative Catalytic Intermediate”
ACS Catal. (2017) 7 – 2367-2373
C. Miceli, J. Rintjema, E. Martin, E.C. Escudero-Adán, C. Zonta, G. Licini, A. W. Kleij

“Synthesis of Carbonates from Alcohols and CO₂”
Top. Curr. Chem. (2017), 375 – 1-28
N. Kindermann, T. Jose, A. W. Kleij

“Mechanistic Insights into the Carbon Dioxide-Cyclohexene Oxide Copolymerization reaction: Is one Metal Center enough?”
ChemSusChem (2017) 10 – 1233-1240
J. González-Fabra, F. Castro-Gómez, A. W. Kleij, C. Bo

“Aluminum-Mediated Formation of Cyclic Carbonates: Benchmarking Catalytic Performance Metrics”
ChemSusChem (2017) 10 – 1274-1282
J. Rintjema, A. W. Kleij

“Recent Progress in Stereoselective Synthesis of Cyclic Organic Carbonates and Beyond”
Curr. Opin. Green Sust. Chem. (2017) 3 – 55-60
J. E. Gómez, A. W. Kleij