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Cordova, Armando
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Publications (10 of 88) Show all publications
Abbaszad Rafi, A., Alimohammadzadeh, R., Avella, A., Mõistlik, T., Jűrisoo, M., Kaaver, A., . . . Cordova, A. (2023). A facile route for concurrent fabrication and surface selective functionalization of cellulose nanofibers by lactic acid mediated catalysis. Scientific Reports, 13(1), Article ID 14730.
Open this publication in new window or tab >>A facile route for concurrent fabrication and surface selective functionalization of cellulose nanofibers by lactic acid mediated catalysis
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2023 (English)In: Scientific Reports, E-ISSN 2045-2322, Vol. 13, no 1, article id 14730Article in journal (Refereed) Published
Abstract [en]

Celulose nanofibers are lightweight, recycable, biodegradable, and renewable. Hence, there is a great interest of using them instead of fossil-based components in new materials and biocomposites. In this study, we disclose an environmentally benign (green) one-step reaction approach to fabricate lactic acid ester functionalized cellulose nanofibrils from wood-derived pulp fibers in high yields. This was accomplished by converting wood-derived pulp fibers to nanofibrillated “cellulose lactate” under mild conditions using lactic acid as both the reaction media and catalyst. Thus, in parallel to the cellulose nanofibril production, concurrent lactic acid-catalyzed esterification of lactic acid to the cellulose nanofibers surface occured. The direct lactic acid esterification, which is a surface selective functionalization and reversible (de-attaching the ester groups by cleavage of the ester bonds), of the cellulose nanofibrils was confirmed by low numbers of degree of substitution, and FT-IR analyses. Thus, autocatalytic esterification and cellulose hydrolysis occurred without the need of metal based or a harsh mineral acid catalysts, which has disadvantages such as acid corrosiveness and high recovery cost of acid. Moreover, adding a mineral acid as a co-catalyst significantly decreased the yield of the nanocellulose. The lactic acid media is successfully recycled in multiple reaction cycles producing the corresponding nanocellulose fibers in high yields. The disclosed green cellulose nanofibril production route is industrial relevant and gives direct access to nanocellulose for use in variety of applications such as sustainable filaments, composites, packaging and strengthening of recycled fibers. 

Place, publisher, year, edition, pages
Springer Nature, 2023
National Category
Paper, Pulp and Fiber Technology
Identifiers
urn:nbn:se:miun:diva-49330 (URN)10.1038/s41598-023-41989-3 (DOI)37679445 (PubMedID)2-s2.0-85170181889 (Scopus ID)
Available from: 2023-09-19 Created: 2023-09-19 Last updated: 2023-09-19Bibliographically approved
Deiana, L., Abbaszad Rafi, A., Tai, C.-W., Bäckvall, J.-E. & Cordova, A. (2023). Artificial Arthropod Exoskeletons/Fungi Cell Walls Integrating Metal and Biocatalysts for Heterogeneous Synergistic Catalysis of Asymmetric Cascade Transformations. ChemCatChem, 15(15)
Open this publication in new window or tab >>Artificial Arthropod Exoskeletons/Fungi Cell Walls Integrating Metal and Biocatalysts for Heterogeneous Synergistic Catalysis of Asymmetric Cascade Transformations
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2023 (English)In: ChemCatChem, ISSN 1867-3880, E-ISSN 1867-3899, Vol. 15, no 15Article in journal (Refereed) Published
Abstract [en]

A novel and sustainable tandem-catalysis system for asymmetric synthesis is disclosed, which is fabricated by bio-inspired self-assembly of artificial arthropod exoskeletons (AAEs) or artificial fungi cell walls (AFCWs) containing two different types of catalysts (enzyme and metal nanoparticles). The heterogeneous integrated enzyme/metal nanoparticle AAE/AFCW systems, which contain chitosan as the main structural component, co-catalyze dynamic kinetic resolution of primary amines via a tandem racemization/enantioselective amidation reaction process to give the corresponding amides in high yields and excellent ee. The heterogeneous AAE/AFCW systems display successful heterogeneous synergistic catalysis at the surfaces since they can catalyze multiple reaction cycles without metal leaching. The use of natural-based and biocompatible structural components makes the AAE/AFCW systems fully biodegradable and renewable, thus fulfilling important green chemistry requirements.

Place, publisher, year, edition, pages
John Wiley & Sons, 2023
Keywords
asymmetric tandem catalysis, chiral amines, chitosan, dynamic kinetic resolution, heterogeneous hybrid catalyst
National Category
Organic Chemistry
Identifiers
urn:nbn:se:miun:diva-49019 (URN)10.1002/cctc.202300250 (DOI)001022816700001 ()2-s2.0-85164018579 (Scopus ID)
Available from: 2023-08-15 Created: 2023-08-15 Last updated: 2023-08-15Bibliographically approved
Deiana, L., Badali, E., Abbaszad Rafi, A., Tai, C.-W., Bäckvall, J.-E. & Cordova, A. (2023). Cellulose-Supported Heterogeneous Gold-Catalyzed Cycloisomerization Reactions of Alkynoic Acids and Allenynamides. ACS Catalysis, 13(15), 10418-10424
Open this publication in new window or tab >>Cellulose-Supported Heterogeneous Gold-Catalyzed Cycloisomerization Reactions of Alkynoic Acids and Allenynamides
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2023 (English)In: ACS Catalysis, ISSN 2155-5435, E-ISSN 2155-5435, Vol. 13, no 15, p. 10418-10424Article in journal (Refereed) Published
Abstract [en]

Herein, we describe efficient nanogold-catalyzed cycloisomerization reactions of alkynoic acids and allenynamides to enol lactones and dihydropyrroles, respectively (the latter via an Alder-ene reaction). The gold nanoparticles were immobilized on thiol-functionalized microcrystalline cellulose and characterized by electron microscopy (HAADF-STEM) and by XPS. The thiol-stabilized gold nanoparticles (Au-0) were obtained in the size range 1.5-6 nm at the cellulose surface. The robust and sustainable cellulose-supported gold nanocatalyst can be recycled for multiple cycles without losing activity.

Place, publisher, year, edition, pages
American Chemical Society (ACS), 2023
Keywords
cellulose-supported nanogold catalysis, C-C bondformation, heterogeneous catalysis, cycloisomerization, heterocycles, Alder-ene reaction
National Category
Organic Chemistry
Identifiers
urn:nbn:se:miun:diva-49539 (URN)10.1021/acscatal.3c02722 (DOI)001066876500001 ()37560186 (PubMedID)2-s2.0-85167895594 (Scopus ID)
Available from: 2023-10-13 Created: 2023-10-13 Last updated: 2023-10-13Bibliographically approved
Alimohammadzadeh, R., Sanhueza, I. & Cordova, A. (2023). Design and fabrication of superhydrophobic cellulose nanocrystal films by combination of self-assembly and organocatalysis. Scientific Reports, 13(1), Article ID 3157.
Open this publication in new window or tab >>Design and fabrication of superhydrophobic cellulose nanocrystal films by combination of self-assembly and organocatalysis
2023 (English)In: Scientific Reports, E-ISSN 2045-2322, Vol. 13, no 1, article id 3157Article in journal (Refereed) Published
Abstract [en]

Cellulose nanocrystals, which have unique properties of high aspect ratio, high surface area, high mechanical strength, and a liquid crystalline nature, constitute a renewable nanomaterial with great potential for several uses (e.g., composites, films and barriers). However, their intrinsic hydrophilicity results in materials that are moisture sensitive and exhibit poor water stability. This limits their use and competitiveness as a sustainable alternative against fossil-based materials/plastics in packaging, food storage, construction and materials application, which cause contamination in our oceans and environment. To make cellulose nanocrystal films superhydrophobic, toxic chemicals such as fluorocarbons are typically attached to their surfaces. Hence, there is a pressing need for environmentally friendly alternatives for their modification and acquiring this important surface property. Herein, we describe the novel creation of superhydrophobic, fluorocarbon-free and transparent cellulose nanocrystal films with functional groups by a bioinspired combination of self-assembly and organocatalytic surface modification at the nanoscale using food approved organic acid catalysts. The resulting film-surface is superhydrophobic (water contact angle > 150°) and has self-cleaning properties (the lotus effect). In addition, the superhydrophobic cellulose nanocrystal films have excellent water stability and significantly decreased oxygen permeability at high relative humidity with oxygen transmission rates better than those of commonly used plastics. 

National Category
Polymer Technologies
Identifiers
urn:nbn:se:miun:diva-47782 (URN)10.1038/s41598-023-29905-1 (DOI)000988352100025 ()36823204 (PubMedID)2-s2.0-85148799074 (Scopus ID)
Available from: 2023-03-13 Created: 2023-03-13 Last updated: 2023-06-26Bibliographically approved
Wu, H., Zheng, Z., Zhang, K., Kajanus, J., Johansson, M. J., Cordova, A. & Bäckvall, J.-E. (2023). Heterogeneous Copper-Catalyzed Cross-Coupling for Sustainable Synthesis of Chiral Allenes: Application to the Synthesis of Allenic Natural Products. Angewandte Chemie International Edition, 62(50), Article ID e202314512.
Open this publication in new window or tab >>Heterogeneous Copper-Catalyzed Cross-Coupling for Sustainable Synthesis of Chiral Allenes: Application to the Synthesis of Allenic Natural Products
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2023 (English)In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 62, no 50, article id e202314512Article in journal (Refereed) Published
Abstract [en]

Classical Crabbé type SN2' substitutions of propargylic substrates has served as one of the standard methods for the synthesis of allenes. However, the stereospecific version of this transformation often requires either stoichiometric amounts of organocopper reagents or special functional groups on the substrates, and the chirality transfer efficiency is also capricious. Herein, we report a sustainable methodology for the synthesis of diverse 1,3-di and tri-substituted allenes by using a simple and cheap cellulose supported heterogeneous nanocopper catalyst (MCC-Amp-Cu(I/II)). This approach represents the first example of heterogeneous catalysis for the synthesis of chiral allenes. High yields and excellent enantiospecificity (up to 97 % yield, 99 % ee) were achieved for a wide range of di- and tri-substituted allenes bearing various functional groups. It is worth noting that the applied heterogeneous catalyst could be recycled at least 5 times without any reduced reactivity. To demonstrate the synthetic utility of the developed protocol, we have applied it to the total synthesis of several chiral allenic natural products. 

Place, publisher, year, edition, pages
Wiley, 2023
Keywords
Allenic Natural Products, Chiral Allenes, Heterogeneous Catalysis, Sustainable Synthesis, Total Synthesis
National Category
Organic Chemistry
Identifiers
urn:nbn:se:miun:diva-49899 (URN)10.1002/anie.202314512 (DOI)001099351500001 ()37899308 (PubMedID)2-s2.0-85176240955 (Scopus ID)
Available from: 2023-11-21 Created: 2023-11-21 Last updated: 2023-12-15Bibliographically approved
Cordova, A., Zhang, K. & Deiana, L. (2023). Organocatalytic Dynamic Kinetic Asymmetric Transformations. In: J.-E Bäckvall (Ed.), Dynamic Kinetic Resolution (DKR) and Dynamic Kinetic Asymmetric Transformations (DYKAT): . Georg Thieme Verlag KG
Open this publication in new window or tab >>Organocatalytic Dynamic Kinetic Asymmetric Transformations
2023 (English)In: Dynamic Kinetic Resolution (DKR) and Dynamic Kinetic Asymmetric Transformations (DYKAT) / [ed] J.-E Bäckvall, Georg Thieme Verlag KG, 2023Chapter in book (Refereed)
Abstract [en]

Dynamic kinetic asymmetric transformations (DYKAT) are an important way of converting simple organic molecules into complex small molecules as single diastereo- and enantiomers. Herein we describe selected examples that are catalyzed by small organic molecules, which utilize activation mechanisms similar to enzymes for accomplishing the high stereoselectivity. The research area of DYKAT is growing and remarkable examples for producing important organic molecules and pharmaceuticals are demonstrated. In this context, organocatalysis will play an important role.

Place, publisher, year, edition, pages
Georg Thieme Verlag KG, 2023
Series
Science of Synthesis
Keywords
dynamic kinetic asymmetric transformation, organocatalysis, highly enantioselective, highly diastereoselective, dual catalysis, hydrogen-bond donation, small-molecule catalysis
National Category
Organic Chemistry
Identifiers
urn:nbn:se:miun:diva-47581 (URN)10.1055/sos-SD-237-00049 (DOI)9783132453777 (ISBN)9783132453791 (ISBN)
Available from: 2023-02-14 Created: 2023-02-14 Last updated: 2023-02-14Bibliographically approved
Veluru, R. N., Abbaszad Rafi, A., Tai, C.-W., Bäckvall, J.-E. & Cordova, A. (2023). Regio- and Stereoselective Carbon-Boron Bond Formation via Heterogeneous Palladium-Catalyzed Hydroboration of Enallenes. Chemistry - A European Journal
Open this publication in new window or tab >>Regio- and Stereoselective Carbon-Boron Bond Formation via Heterogeneous Palladium-Catalyzed Hydroboration of Enallenes
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2023 (English)In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765Article in journal (Refereed) Published
Abstract [en]

A highly efficient regio- and stereoselective heterogeneous palladium-catalyzed hydroboration reaction of enallenes was developed. Nanopalladium immobilized on microcrystalline cellulose (MCC) was successfully employed as an efficient catalyst for the enallene hydroboration reaction. The nanopalladium particles were shown by HAADF-STEM to have an average size of 2.4 nm. The cellulose-supported palladium catalyst exhibits high stability and provides vinyl boron products in good to high isolated yields (up to 90 %). The nanopalladium catalyst can be efficiently recycled and it was demonstrated that the catalyst can be used in 7 runs with a maintained high yield (>80 %). The vinylboron compounds prepared from enallenes are important synthetic intermediates that can be used in various organic synthetic transformations. 

Keywords
cellulose, enallenes, heterogeneous catalysis, palladium, regio- and stereoselective hydroboration
National Category
Organic Chemistry
Identifiers
urn:nbn:se:miun:diva-48009 (URN)10.1002/chem.202203950 (DOI)000953617500001 ()2-s2.0-85150410152 (Scopus ID)
Available from: 2023-03-28 Created: 2023-03-28 Last updated: 2023-04-27Bibliographically approved
Deiana, L., Abbaszad Rafi, A., Bäckvall, J.-E. & Cordova, A. (2023). Subtilisin integrated artificial plant cell walls as heterogeneous catalysts for asymmetric synthesis of (S)-amides. RSC Advances, 13(29), 19975-19980
Open this publication in new window or tab >>Subtilisin integrated artificial plant cell walls as heterogeneous catalysts for asymmetric synthesis of (S)-amides
2023 (English)In: RSC Advances, E-ISSN 2046-2069, Vol. 13, no 29, p. 19975-19980Article in journal (Refereed) Published
Abstract [en]

Subtilisin integrated artificial plant-cell walls (APCWs) were fabricated by self-assembly using cellulose or nanocellulose as the main component. The resulting APCW catalysts are excellent heterogeneous catalysts for the asymmetric synthesis of (S)-amides. This was demonstrated by the APCW-catalyzed kinetic resolution of several racemic primary amines to give the corresponding (S)-amides in high yields with excellent enantioselectivity. The APCW catalyst can be recycled for multiple reaction cycles without loss of enantioselectivity. The assembled APCW catalyst was also able to cooperate with a homogeneous organoruthenium complex, which allowed for the co-catalytic dynamic kinetic resolution (DKR) of a racemic primary amine to give the corresponding (S)-amide in high yield. The APCW/Ru co-catalysis constitutes the first examples of DKR of chiral primary amines when subtilisin is used as a co-catalyst.

Place, publisher, year, edition, pages
Royal Society of Chemistry (RSC), 2023
National Category
Organic Chemistry
Identifiers
urn:nbn:se:miun:diva-49034 (URN)10.1039/d3ra02193a (DOI)001022295400001 ()37404321 (PubMedID)2-s2.0-85165532562 (Scopus ID)
Available from: 2023-08-15 Created: 2023-08-15 Last updated: 2023-08-15Bibliographically approved
Zhang, K., Carmo, C., Deiana, L., Svensson Grape, E., Inge, A. K. & Córdova, A. (2023). Sugar-Assisted Kinetic Resolutions in Metal/Chiral Amine Co-Catalyzed α-Allylations and [4+2] Cycloadditions: Highly Enantioselective Synthesis of Sugar and Chromane Derivatives. Chemistry - A European Journal, 29(53)
Open this publication in new window or tab >>Sugar-Assisted Kinetic Resolutions in Metal/Chiral Amine Co-Catalyzed α-Allylations and [4+2] Cycloadditions: Highly Enantioselective Synthesis of Sugar and Chromane Derivatives
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2023 (English)In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 29, no 53Article in journal (Refereed) Published
Abstract [en]

Functionalized triose-, furanose and chromane-derivatives were synthesized by the titled reactions. The sugar-assisted kinetic resolution/C−C bond-forming cascade processes generate a functionalized sugar derivative with a quaternary stereocenter in a highly enantioselective fashion (up to >99 % ee) by using a simple combination of metal and chiral amine co-catalysts. Notably, the interplay between the chiral sugar substrate and the chiral amino acid derivative allowed for the construction of a functionalized sugar product with high enantioselectivity (up to 99 %) also when using a combination of racemic amine catalyst (0 % ee) and metal catalyst. 

Place, publisher, year, edition, pages
Wiley, 2023
Keywords
enantioselective α-allylations, functionalized sugar derivatives, sugar-assisted, synergistic co-catalysis, [4+2] cycloaddition
National Category
Organic Chemistry
Identifiers
urn:nbn:se:miun:diva-49185 (URN)10.1002/chem.202301725 (DOI)001052249800001 ()2-s2.0-85168369803 (Scopus ID)
Available from: 2023-08-29 Created: 2023-08-29 Last updated: 2023-09-21Bibliographically approved
Alimohammadzadeh, R., Abbaszad Rafi, A., Goclik, L., Tai, C.-W. & Cordova, A. (2022). Direct Organocatalytic Thioglycolic Acid Esterification of Cellulose Nanocrystals: A simple entry to click chemistry on the surface of nanocellulose. Carbohydrate Polymer Technologies and Applications, 3, Article ID 100205.
Open this publication in new window or tab >>Direct Organocatalytic Thioglycolic Acid Esterification of Cellulose Nanocrystals: A simple entry to click chemistry on the surface of nanocellulose
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2022 (English)In: Carbohydrate Polymer Technologies and Applications, ISSN 2666-8939, Vol. 3, article id 100205Article in journal (Refereed) Published
Abstract [en]

The mild and simple direct organocatalytic esterification of cellulose nanocrystals (CNC) and nanocellulose-based materials (e.g. foams and films) with thioglycolic acid (TGA) is disclosed. The transformation gives the corresponding thiol group (-SH) functionalized crystalline nanocellulose (CNC-SH) using simple, naturally occurring, and non-toxic organic acids (e.g. tartaric acid) as catalysts. We also discovered that the direct esterification of cellulose with TGA is autocatalytic (i.e. the TGA is catalyzing its own esterification). The introduction of the -SH functionality at the nanocellulose surface opens up for further selective applications. This was demonstrated by attaching organic catalysts and fluorescent molecules, which are useful as sensors, to the CNC-SH surface by thiol-ene click chemistry. Another application is to use the CNC-SH-based foam as a heterogeneous biomimetic reducing agent, which is stable during multiple recycles, for the copper-catalyzed alkyne-azide 1,3-dipolar cycloaddition (“click” reaction).

Keywords
Cellulose nanocrystals, Thiol-functionalized nanocellulose, Organocatalysis, Heterogeneous catalysis, Direct esterification, Click chemistry
National Category
Natural Sciences Bio Materials
Identifiers
urn:nbn:se:miun:diva-41923 (URN)10.1016/j.carpta.2022.100205 (DOI)000821577600041 ()2-s2.0-85129227500 (Scopus ID)
Available from: 2023-01-01 Created: 2021-04-22 Last updated: 2023-02-14Bibliographically approved
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