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Publications (10 of 234) Show all publications
Wang, B., Ren, M., Iqbal, N., Mu, X., Bäckvall, J.-E. & Yang, B. (2024). Palladium-Catalyzed Dehydrogenative Carbonylative Esterification of Allenoic Acids for the Synthesis of γ-Butyrolactone Derivatives. Organic Letters, 26(12), 2430-2434
Open this publication in new window or tab >>Palladium-Catalyzed Dehydrogenative Carbonylative Esterification of Allenoic Acids for the Synthesis of γ-Butyrolactone Derivatives
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2024 (English)In: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 26, no 12, p. 2430-2434Article in journal (Refereed) Published
Abstract [en]

A highly efficient dehydrogenative carbonylative esterification of allenoic acids using Pd-catalysis was developed, providing a novel approach to synthesizing esterified γ-butyrolactone derivatives with consistently good to excellent results demonstrated across over 50 examples. Additionally, we used a heterogeneous catalyst known as Pd-AmP-MCF and harnessed biomimetic-aerobic-oxidation conditions to facilitate the practical execution of this reaction. Furthermore, our detailed study of γ-butyrolactone products highlighted their potential in synthesizing bioactive compounds.

National Category
Organic Chemistry
Identifiers
urn:nbn:se:su:diva-227811 (URN)10.1021/acs.orglett.4c00572 (DOI)001187631300001 ()38502799 (PubMedID)2-s2.0-85188247978 (Scopus ID)
Available from: 2024-04-05 Created: 2024-04-05 Last updated: 2024-04-29Bibliographically approved
Deiana, L., Rafi, A. 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), Article ID e202300250.
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 15, article id e202300250Article 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. 

Keywords
asymmetric tandem catalysis, chiral amines, chitosan, dynamic kinetic resolution, heterogeneous hybrid catalyst
National Category
Chemical Process Engineering
Identifiers
urn:nbn:se:su:diva-221309 (URN)10.1002/cctc.202300250 (DOI)001022816700001 ()2-s2.0-85164018579 (Scopus ID)
Available from: 2023-09-19 Created: 2023-09-19 Last updated: 2023-09-21Bibliographically approved
Deiana, L., Badali, E., Rafi, A. 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.

Keywords
cellulose-supported nanogold catalysis, C-C bondformation, heterogeneous catalysis, cycloisomerization, heterocycles, Alder-ene reaction
National Category
Organic Chemistry
Identifiers
urn:nbn:se:su:diva-223193 (URN)10.1021/acscatal.3c02722 (DOI)001066876500001 ()37560186 (PubMedID)2-s2.0-85167895594 (Scopus ID)
Available from: 2023-10-24 Created: 2023-10-24 Last updated: 2023-10-24Bibliographically approved
Wu, H., Zheng, Z., Zhang, K., Kajanus, J., Johansson, M. J., Córdova, 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. 

Keywords
Allenic Natural Products, Chiral Allenes, Heterogeneous Catalysis, Sustainable Synthesis, Total Synthesis
National Category
Organic Chemistry
Identifiers
urn:nbn:se:su:diva-224606 (URN)10.1002/anie.202314512 (DOI)001099351500001 ()37899308 (PubMedID)2-s2.0-85176240955 (Scopus ID)
Available from: 2023-12-22 Created: 2023-12-22 Last updated: 2023-12-22Bibliographically approved
Bermejo-López, A., Kong, W.-J., Tortajada, P. J., Posevins, D., Martín‐Matute, B. & Bäckvall, J.-E. (2023). Iron-Catalyzed Borylation of Propargylic Acetates for the Synthesis of Multisubstituted Allenylboronates. Chemistry - A European Journal, 29(3), Article ID e202203130.
Open this publication in new window or tab >>Iron-Catalyzed Borylation of Propargylic Acetates for the Synthesis of Multisubstituted Allenylboronates
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2023 (English)In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 29, no 3, article id e202203130Article in journal (Refereed) Published
Abstract [en]

A novel iron-catalyzed borylation of propargylic acetates leading to allenylboronates has been developed. The method allows the preparation of a variety of di-, tri- and tetrasubstituted allenylboronates at room temperature with good functional group compatibility. Stereochemical studies show that an anti-SN2’ displacement of acetate by boron occurs; this also allows transfer of chirality to yield enantiomerically enriched allenylboronates. The synthetic utility of this protocol was further substantiated by transformations of the obtained allenylboronates including oxidation and propargylation. 

Keywords
Allenes, allenylboronates, borylation, iron, propargyl esters
National Category
Chemical Sciences
Identifiers
urn:nbn:se:su:diva-213118 (URN)10.1002/chem.202203130 (DOI)000888153700001 ()36250587 (PubMedID)2-s2.0-85143203381 (Scopus ID)
Available from: 2022-12-20 Created: 2022-12-20 Last updated: 2023-02-23Bibliographically approved
Kong, W.-J., Kessler, S. N., Wu, H. & Bäckvall, J.-E. (2023). Iron-Catalyzed Cross-Coupling of α-Allenyl Esters with Grignard Reagents for the Synthesis of 1,3-Dienes. Organic Letters, 25(1), 120-124
Open this publication in new window or tab >>Iron-Catalyzed Cross-Coupling of α-Allenyl Esters with Grignard Reagents for the Synthesis of 1,3-Dienes
2023 (English)In: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 25, no 1, p. 120-124Article in journal (Refereed) Published
Abstract [en]

Structurally diverse 1,3-dienes are valuable building blocks in organic synthesis. Herein we report the iron-catalyzed coupling between α-allenyl esters and Grignard reagents, which provides a fast and practical approach to a variety of complex substituted 1,3-dienes. The reaction involves an inexpensive iron catalyst, mild reaction conditions, and provides easy scale up. 

National Category
Chemical Sciences
Identifiers
urn:nbn:se:su:diva-214336 (URN)10.1021/acs.orglett.2c03916 (DOI)000910948000001 ()36599130 (PubMedID)2-s2.0-85146042130 (Scopus ID)
Available from: 2023-02-06 Created: 2023-02-06 Last updated: 2023-02-06Bibliographically approved
Manna, S., Peters, J., Bermejo-López, A., Himo, F. & Bäckvall, J.-E. (2023). Mechanistic Studies on Iron-Catalyzed Dehydrogenation of Amines Involving Cyclopentadienone Iron Complexes-Evidence for Stepwise Hydride and Proton Transfer. ACS Catalysis, 13(13), 8477-8484
Open this publication in new window or tab >>Mechanistic Studies on Iron-Catalyzed Dehydrogenation of Amines Involving Cyclopentadienone Iron Complexes-Evidence for Stepwise Hydride and Proton Transfer
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2023 (English)In: ACS Catalysis, E-ISSN 2155-5435, Vol. 13, no 13, p. 8477-8484Article in journal (Refereed) Published
Abstract [en]

The mechanism of dehydrogenation of amines catalyzedby (cyclopentadienone)ironcarbonyl complexes was studied by means of kinetic isotope effect(KIE) measurements, intermediate isolation, and density functionaltheory calculations. The (cyclopentadienone)iron-amine intermediateswere isolated and characterized by H-1 and C-13 NMR spectroscopy as well as X-ray crystallography. The isolatediron-amine complexes are quite stable and undergo a formal beta-hydride elimination to produce imine and iron hydride complexes.The KIEs observed for the iron-catalyzed dehydrogenation of 4-methoxy-N-(4-methylbenzyl)aniline are in accordance with stepwisedehydrogenation. The density functional calculations corroborate astepwise mechanism involving a rate-determining hydride transfer fromamine to iron to yield a metal hydride and an iminium intermediate,followed by a proton transfer from the iminium ion to the oxygen ofthe cyclopentadienone ligand.

Keywords
iron catalysis, dehydrogenation, amines, hydrogen transfer, kinetic isotope effects, DFT calculations
National Category
Biochemistry and Molecular Biology
Identifiers
urn:nbn:se:su:diva-229560 (URN)10.1021/acscatal.3c01779 (DOI)001004328500001 ()
Available from: 2024-05-24 Created: 2024-05-24 Last updated: 2024-05-24Bibliographically approved
Ramesh Naidu, V., Rafi, A. A., Tai, C.-W., Bäckvall, J. E. & Córdova, A. (2023). Regio- and Stereoselective Carbon-Boron Bond Formation via Heterogeneous Palladium-Catalyzed Hydroboration of Enallenes. Chemistry - A European Journal, 29(24), Article ID e202203950.
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 1521-3765, Vol. 29, no 24, article id e202203950Article 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:su:diva-216462 (URN)10.1002/chem.202203950 (DOI)000953617500001 ()36719323 (PubMedID)2-s2.0-85150410152 (Scopus ID)
Available from: 2023-05-02 Created: 2023-05-02 Last updated: 2023-09-22Bibliographically approved
Deiana, L., Rafi, A. 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.

National Category
Chemical Sciences
Identifiers
urn:nbn:se:su:diva-221327 (URN)10.1039/d3ra02193a (DOI)001022295400001 ()37404321 (PubMedID)2-s2.0-85165532562 (Scopus ID)
Available from: 2023-09-19 Created: 2023-09-19 Last updated: 2023-09-19Bibliographically approved
Zheng, Z., Deiana, L., Posevins, D., Rafi, A. A., Zhang, K., Johansson, M. J., . . . Bäckvall, J.-E. (2022). Efficient Heterogeneous Copper-Catalyzed Alder-Ene Reaction of Allenynamides to Pyrrolines. ACS Catalysis, 12(3), 1791-1796
Open this publication in new window or tab >>Efficient Heterogeneous Copper-Catalyzed Alder-Ene Reaction of Allenynamides to Pyrrolines
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2022 (English)In: ACS Catalysis, ISSN 2155-5435, E-ISSN 2155-5435, Vol. 12, no 3, p. 1791-1796Article in journal (Refereed) Published
Abstract [en]

Herein, we describe an efficient nanocopper-catalyzed Alder-ene reaction of allenynamides. The copper nanoparticles were immobilized on amino-functionalized microcrystalline cellulose. A solvent-controlled chemoselectivity of the reaction was observed, leading to the chemodivergent synthesis of pyrrolines (2,5-dihydropyrroles) and pyrroles. The heterogeneous copper catalyst exhibits high efficiency and good recyclability in the Alder-ene reaction, constituting a highly attractive catalytic system from an economical and environmental point of view. 

Keywords
cellulose, heterogeneous, nanocopper, Alder-ene reaction, pyrrolines
National Category
Chemical Sciences
Identifiers
urn:nbn:se:su:diva-202043 (URN)10.1021/acscatal.1c05147 (DOI)000745221000001 ()
Available from: 2022-02-10 Created: 2022-02-10 Last updated: 2022-03-23Bibliographically approved
Organisations
Identifiers
ORCID iD: ORCID iD iconorcid.org/0000-0001-8462-4176

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