Kleij
Research group
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 features. Our targeted portfolio of organic structures include oxazolidinones, CO2-based (bio)polymers and more complex organic matter derived from stereo-selective or enantioselective coupling approaches; examples are substituted allylic compounds and chiral amino acid derivatives. An important part of our work puts attention to new catalyst design and efforts to reach a higher level of understanding concerning the observed reactivity/selectivity features by means of mechanistic and computational studies. Collaborations with the industrial sector having interest in bio-based polymers form also part of our work in order to be able to transfer technological advancements from bench to and beyond pilot scale.
Topics addressed
- CO2 to Carbonates
- CO2 to Fine Chemicals:
- CO2/Renewables to Polymers:
Articles
“Palladium-Catalyzed Stereoselective Formation of Substituted Allylic Thioethers and Sulfones”
Org. Lett. (2016) 18 – 6042-6045
José Enrique Gómez, Wusheng Guo, Arjan W. Kleij*
“Palladium-Catalyzed Regio- and Enantio-Selective Synthesis of Allylic Amines Featuring Tetrasubstituted Tertiary Carbons”
J. Am. Chem. Soc. (2016) 138 – 14194-14197
Aijie Cai, Wusheng Guo*, Luis MartĂnez-RodrĂguez, Arjan W. Kleij*
“Aluminum Catalyzed formation of Functional 1,3,2-Dioxathiolane 2-Oxides from Sulfur Dioxide: An Easy Entry towards N-Substituted Aziridines“
Adv. Synth. Catal. (2016) 358 – 3832-3839
Victor Laserna, Eddy Martin, Eduardo C. Escudero-Adán and Arjan W. Kleij*
“Terpolymers derived from Limonene Oxide and Carbon Dioxide: Access to Cross-Linked Polycarbonates with Improved Thermal Properties”
Macromolecules (2016) 49 – 6285-6295
Carmen MartĂn, Arjan W. Kleij
“Stereoselective and Versatile Preparation of Tri- and Tetra-Substituted Allylic Amine Scaffolds under Mild Conditions”
J. Am. Chem. Soc. (2016) 138 – 11970-11978.
Wusheng Guo, Luis MartĂnez-RodrĂguez, Rositha Kuniyil, Eddy Martin, Eduardo C. Escudero-Adán, Feliu Maseras*, Arjan W. Kleij*
“Alternating Copolymerization of Propylene Oxide and Cyclohexene Oxide with Tricyclic Anhydrides: Access to Partially Renewable Aliphatic Polyesters with High Glass Transition Temperatures”
Macromolecules (2016) 49 – 6394-6400
M. J. Sanford, L. Peña Carrodeaguas, N. J. Van Zee, A. W. Kleij*, G. W. Coates*
“Substrate-Assisted Carbon Dioxide Activation as a Versatile Approach for Heterocyclic Synthesis”
Synthesis (2016) 48 – 3863-3878
J. Rintjema, A. W. Kleij*
“Highly Efficient Catalytic Formation of (Z)-1,4-But-2-ene Diols using Water as a Nucleophile”
Angew. Chem. Int. Ed. (2016) 55 – 11037-11040
W. Guo, L. MartĂnez-RodrĂguez, E. MartĂn, E. C. Escudero-Adán, A. W. Kleij*
“Catalytic Coupling of Carbon Dioxide with Terpene Scaffolds: Access to Challenging Bio-Based Organic Carbonates“
ChemSusChem (2016) 9 – 1304-1311
G. Fiorani*, M. Stuck, C. MartĂn, M. MartĂnez-Belmonte, E. Martin, E. C. Escudero-Adán, A. W. Kleij*
“Regioselective Organocatalytic Formation of Carbamates from Substituted Cyclic Carbonates”
Adv. Synth. Catal. (2016) 358 – 2172-2178
S. Sopeña, V. Laserna, W. Guo, E. Martin, E. C. Escudero-Adán, A. W. Kleij*
“Substrate Controlled Product Divergence in CO2 Conversion to Heterocyclic Products”
Angew. Chem. Int. Ed. (2016) 55 – 3972-3976
J. Rintjema, R. Epping, G. Fiorani, E. MartĂn, E. C. Escudero-Adán, A. W. Kleij*
“Cavitand based Polyphenols as Highly Reactive Organocatalysts for the Coupling of Carbon Dioxide and Oxiranes”
ChemSusChem (2016) 9 – 749-755
L. MartĂnez-RodrĂguez, J. Otalora Garmilla, A. W. Kleij*
“Stereodivergent Carbamate Synthesis by Selective in Situ Trapping of Organic Carbonate Intermediates”
Chem. Eur. J. (2016) 22 – 1722-1727
W. Guo, V. Laserna, E. Martin, E. C. Escudero-Adán, A. W. Kleij *
“Catalytic One-Pot Oxetane to Carbamate Conversions: Formal Synthesis of Drug Relevant Molecules”
Adv. Synth. Catal. (2016) 358 – 1602-1607
W. Guo, V. Laserna, J. Rintjema, A. W. Kleij*
“Iron Complex Based catalysts”, in: “Sustainable Catalysis: Volume 1: Catalysis by Non-Endangered Metals”, Ed. Michael North, Royal Society of Chemistry, 2016, 13, 373-406, (ISBN: 9781782620563)
A. W. Kleij*, L. MartĂnez-RodrĂguez, G. Fiorani, C. MartĂn
“Metal Complexes Catalyzed Cyclization with CO2” in “Topics in Organometallic Chemistry, 53”, Ed. Xiao-Bing Lu, Springer, 2016, 2, 39-17, (ISBN: 1436-6002)
J. Rintjema, L. Peña Carrodeguas, V. Laserna, S. Sopeña, A. W. Kleij*