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  1. Article ; Online: The Choice of Rhodium Catalysts in [2+2+2] Cycloaddition Reaction: A Personal Account.

    Pla-Quintana, Anna / Roglans, Anna

    Molecules (Basel, Switzerland)

    2022  Volume 27, Issue 4

    Abstract: 2+2+2] Cycloaddition reaction is a captivating process that assembles six-membered rings from three unsaturations with complete atom economy. Of the multiple transition metals that can be used to catalyze this reaction, rhodium offers many advantages. ... ...

    Abstract [2+2+2] Cycloaddition reaction is a captivating process that assembles six-membered rings from three unsaturations with complete atom economy. Of the multiple transition metals that can be used to catalyze this reaction, rhodium offers many advantages. These include high activity and versatility, but especially the ability to easily tune the reactivity and selectivity by the modification of the ligands around the metal. In this personal account, we summarize our endeavours in the development of efficient and sustainable [2+2+2] cycloaddition reactions to prepare products of interest, develop conditions in which the catalyst can be recovered and reused, and understand the mechanistic details that govern the selectivity of the processes.
    Language English
    Publishing date 2022-02-16
    Publishing country Switzerland
    Document type Journal Article ; Review
    ZDB-ID 1413402-0
    ISSN 1420-3049 ; 1431-5165 ; 1420-3049
    ISSN (online) 1420-3049
    ISSN 1431-5165 ; 1420-3049
    DOI 10.3390/molecules27041332
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    In stock of ZB MED Cologne/Königswinter

    Zs.MO 81: Show issues

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  2. Article: Unveiling the regioselectivity of rhodium(I)-catalyzed [2 + 2 + 2] cycloaddition reactions for open-cage C

    Castanyer, Cristina / Pla-Quintana, Anna / Roglans, Anna / Artigas, Albert / Solà, Miquel

    Beilstein journal of organic chemistry

    2024  Volume 20, Page(s) 272–279

    Abstract: The regioselective functionalization of fullerenes holds significant promise for applications in the fields of medicinal chemistry, materials science, and photovoltaics. In this study, we investigate the regioselectivity of the rhodium(I)-catalyzed [2 + ... ...

    Abstract The regioselective functionalization of fullerenes holds significant promise for applications in the fields of medicinal chemistry, materials science, and photovoltaics. In this study, we investigate the regioselectivity of the rhodium(I)-catalyzed [2 + 2 + 2] cycloaddition reactions between diynes and C
    Language English
    Publishing date 2024-02-13
    Publishing country Germany
    Document type Journal Article
    ZDB-ID 2192461-2
    ISSN 1860-5397
    ISSN 1860-5397
    DOI 10.3762/bjoc.20.28
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  3. Article ; Online: The Choice of Rhodium Catalysts in [2+2+2] Cycloaddition Reaction

    Anna Pla-Quintana / Anna Roglans

    Molecules, Vol 27, Iss 1332, p

    A Personal Account

    2022  Volume 1332

    Abstract: 2+2+2] Cycloaddition reaction is a captivating process that assembles six-membered rings from three unsaturations with complete atom economy. Of the multiple transition metals that can be used to catalyze this reaction, rhodium offers many advantages. ... ...

    Abstract [2+2+2] Cycloaddition reaction is a captivating process that assembles six-membered rings from three unsaturations with complete atom economy. Of the multiple transition metals that can be used to catalyze this reaction, rhodium offers many advantages. These include high activity and versatility, but especially the ability to easily tune the reactivity and selectivity by the modification of the ligands around the metal. In this personal account, we summarize our endeavours in the development of efficient and sustainable [2+2+2] cycloaddition reactions to prepare products of interest, develop conditions in which the catalyst can be recovered and reused, and understand the mechanistic details that govern the selectivity of the processes.
    Keywords rhodium ; catalysis ; [2+2+2] cycloadditions ; Organic chemistry ; QD241-441
    Language English
    Publishing date 2022-02-01T00:00:00Z
    Publisher MDPI AG
    Document type Article ; Online
    Database BASE - Bielefeld Academic Search Engine (life sciences selection)

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  4. Article ; Online: Unveiling the Reaction Mechanisms of the Synthesis and the Excited State Intramolecular Proton Transfer of 2-(2'-hydroxyphenyl)imidazo[1,2-a]pyridine.

    Monreal-Corona, Roger / Stasyuk, Anton J / Solà, Miquel / Pla-Quintana, Anna / Poater, Albert

    Chemphyschem : a European journal of chemical physics and physical chemistry

    2024  Volume 25, Issue 8, Page(s) e202400069

    Abstract: Given its wide variety of applications in the pharmaceutical industry, the synthesis of imidazo[1,2-a]pyridines has been extensively studied since the beginning of the last century. Here, we disclose the mechanism for the synthesis of imidazo[1,2-a] ... ...

    Abstract Given its wide variety of applications in the pharmaceutical industry, the synthesis of imidazo[1,2-a]pyridines has been extensively studied since the beginning of the last century. Here, we disclose the mechanism for the synthesis of imidazo[1,2-a]pyridines by means of the Ortoleva-King reaction. We also reveal the reaction pathway leading to the formation of a iodinated byproduct, demonstrating the challenge of preventing the formation of such a byproduct because of the low energy barrier to access it. Moreover, quantum chemistry tools were employed to investigate the mechanism of intramolecular proton transfer in the excited state, and connections with aromaticity were explored.
    Language English
    Publishing date 2024-03-05
    Publishing country Germany
    Document type Journal Article
    ZDB-ID 2025223-7
    ISSN 1439-7641 ; 1439-4235
    ISSN (online) 1439-7641
    ISSN 1439-4235
    DOI 10.1002/cphc.202400069
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  5. Article ; Online: Stereoretentive Formation of Cyclobutanes from Pyrrolidines: Lessons Learned from DFT Studies of the Reaction Mechanism.

    Monreal-Corona, Roger / Solà, Miquel / Pla-Quintana, Anna / Poater, Albert

    The Journal of organic chemistry

    2023  Volume 88, Issue 7, Page(s) 4619–4626

    Abstract: The stereoselective synthesis of cyclobutanes that possess an array of stereocenters in a contiguous fashion has attracted the wide interest of the synthetic community. Cyclobutanes can be generated from the contraction of pyrrolidines through the ... ...

    Abstract The stereoselective synthesis of cyclobutanes that possess an array of stereocenters in a contiguous fashion has attracted the wide interest of the synthetic community. Cyclobutanes can be generated from the contraction of pyrrolidines through the formation of 1,4-biradical intermediates. Little else is known about the reaction mechanism of this reaction. Here, we unveil the mechanism for this stereospecific synthesis of cyclobutanes by means of density functional theory (DFT) calculations. The rate-determining step of this transformation corresponds to the release of N
    Language English
    Publishing date 2023-03-20
    Publishing country United States
    Document type Journal Article
    ZDB-ID 123490-0
    ISSN 1520-6904 ; 0022-3263
    ISSN (online) 1520-6904
    ISSN 0022-3263
    DOI 10.1021/acs.joc.3c00080
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    In stock of ZB MED Cologne/Königswinter

    Zs.A 4473: Show issues Location:
    Je nach Verfügbarkeit (siehe Angabe bei Bestand)
    bis Jg. 1994: Bestellungen von Artikeln über das Online-Bestellformular
    Jg. 1995 - 2021: Lesesall (2.OG)
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  6. Article: Rh(I) Complexes with Hemilabile Thioether-Functionalized NHC Ligands as Catalysts for [2 + 2 + 2] Cycloaddition of 1,5-Bisallenes and Alkynes.

    Vila, Jordi / Solà, Miquel / Achard, Thierry / Bellemin-Laponnaz, Stéphane / Pla-Quintana, Anna / Roglans, Anna

    ACS catalysis

    2023  Volume 13, Issue 5, Page(s) 3201–3210

    Abstract: The [2 + 2 + 2] cycloaddition of 1,5-bisallenes and alkynes under the catalysis of Rh(I) with hemilabile thioether-functionalized N-heterocyclic carbene ligands is described. This protocol effectively provides an entry to ... ...

    Abstract The [2 + 2 + 2] cycloaddition of 1,5-bisallenes and alkynes under the catalysis of Rh(I) with hemilabile thioether-functionalized N-heterocyclic carbene ligands is described. This protocol effectively provides an entry to different
    Language English
    Publishing date 2023-02-17
    Publishing country United States
    Document type Journal Article
    ISSN 2155-5435
    ISSN 2155-5435
    DOI 10.1021/acscatal.2c05790
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  7. Article ; Online: Highly Selective Synthesis of Seven-Membered Azaspiro Compounds by a Rh(I)-Catalyzed Cycloisomerization/Diels-Alder Cascade of 1,5-Bisallenes.

    Vila, Jordi / Solà, Miquel / Pla-Quintana, Anna / Roglans, Anna

    The Journal of organic chemistry

    2022  Volume 87, Issue 8, Page(s) 5279–5286

    Abstract: The synthesis of spiro compounds featuring seven- and six-membered rings in the spirobicyclic motif is successfully achieved through a cascade process encompassing a rhodium(I)-catalyzed cycloisomerization followed by a highly selective Diels-Alder ... ...

    Abstract The synthesis of spiro compounds featuring seven- and six-membered rings in the spirobicyclic motif is successfully achieved through a cascade process encompassing a rhodium(I)-catalyzed cycloisomerization followed by a highly selective Diels-Alder homodimerization. The scope of the reaction is analyzed based on a series of synthetic substrates, and control experiments and DFT calculations led us to justify the exquisite degree of selectivity observed.
    MeSH term(s) Catalysis ; Density Functional Theory ; Rhodium/chemistry
    Chemical Substances Rhodium (DMK383DSAC)
    Language English
    Publishing date 2022-03-24
    Publishing country United States
    Document type Journal Article ; Research Support, Non-U.S. Gov't
    ZDB-ID 123490-0
    ISSN 1520-6904 ; 0022-3263
    ISSN (online) 1520-6904
    ISSN 0022-3263
    DOI 10.1021/acs.joc.2c00065
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    In stock of ZB MED Cologne/Königswinter

    Zs.A 4473: Show issues Location:
    Je nach Verfügbarkeit (siehe Angabe bei Bestand)
    bis Jg. 1994: Bestellungen von Artikeln über das Online-Bestellformular
    Jg. 1995 - 2021: Lesesall (2.OG)
    ab Jg. 2022: Lesesaal (EG)

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  8. Article ; Online: Copper(I) Iodide Catalyzed [3 + 3] Annulation of Iodonium Ylides with Pyridinium 1,4-Zwitterionic Thiolates for the Synthesis of 1,4-Oxathiin Scaffolds.

    Díaz-Jiménez, Àlex / Kennington, Stuart C D / Roglans, Anna / Pla-Quintana, Anna

    Organic letters

    2023  Volume 25, Issue 26, Page(s) 4830–4834

    Abstract: The selective assembly of the 1,4-oxathiin nucleus has been treated as a powerful strategy to access this scaffold present in molecules with very interesting properties. In this study, the chameleon-like reactivity of pyridinium 1,4-zwitterionic ... ...

    Abstract The selective assembly of the 1,4-oxathiin nucleus has been treated as a powerful strategy to access this scaffold present in molecules with very interesting properties. In this study, the chameleon-like reactivity of pyridinium 1,4-zwitterionic thiolates is exploited to assemble the 1,4-oxathiin core through a [3 + 3] annulation. The optimal annulation partner has been found to be the iodonium ylide of the cyclic 1,3-diketones. The developed protocol allows the synthesis of a variety of bicyclic 1,4-oxathiin derivatives under very mild conditions under copper(I) iodide catalysis. Access to benzoannulated 1,4-oxathiins has been achieved through iodine-mediated aromatization of the initially obtained bicyclic compounds.
    Language English
    Publishing date 2023-06-26
    Publishing country United States
    Document type Journal Article
    ISSN 1523-7052
    ISSN (online) 1523-7052
    DOI 10.1021/acs.orglett.3c01538
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  9. Article ; Online: Photoredox catalysis leading to triazolo-quinoxalinones at room temperature: selectivity of the rate determining step.

    Monreal-Corona, Roger / Besalú, Emili / Pla-Quintana, Anna / Poater, Albert

    Organic & biomolecular chemistry

    2022  Volume 20, Issue 47, Page(s) 9330–9336

    Abstract: The interest in the fusion product of quinoxalinone skeletons and 1,2,3-triazole units has greatly increased in recent years since they are known to be agonists of G-protein-coupled Niacin receptor 109A and inhibitors of the benzodiazepine and adenosine ... ...

    Abstract The interest in the fusion product of quinoxalinone skeletons and 1,2,3-triazole units has greatly increased in recent years since they are known to be agonists of G-protein-coupled Niacin receptor 109A and inhibitors of the benzodiazepine and adenosine receptors. Here, we unveil the mechanism for the photoredox catalyzed synthesis of those scaffolds by means of DFT calculations. The calculations indicate that the rate determining step of this transformation is the attack of the
    Language English
    Publishing date 2022-12-07
    Publishing country England
    Document type Journal Article
    ZDB-ID 2097583-1
    ISSN 1477-0539 ; 1477-0520
    ISSN (online) 1477-0539
    ISSN 1477-0520
    DOI 10.1039/d2ob01587k
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  10. Article ; Online: Mechanistic Studies of Transition-Metal-Catalyzed [2 + 2 + 2] Cycloaddition Reactions.

    Roglans, Anna / Pla-Quintana, Anna / Solà, Miquel

    Chemical reviews

    2020  Volume 121, Issue 3, Page(s) 1894–1979

    Abstract: The development of catalytic methodologies involving the formation of C-C bonds to enable the generation of cyclic systems constitutes a field of great relevance in synthetic organic chemistry. One paradigmatic process to accomplish this goal efficiently ...

    Abstract The development of catalytic methodologies involving the formation of C-C bonds to enable the generation of cyclic systems constitutes a field of great relevance in synthetic organic chemistry. One paradigmatic process to accomplish this goal efficiently is the transition-metal-catalyzed [2 + 2 + 2] cycloaddition reaction, since it permits the formation of a wide range of highly functionalized 6-membered carbo- and heterocyclic molecules in a single step with high efficiency and perfect atom economy. A key feature of these transformations is the mechanistic pathway that they follow, since a deep knowledge of this mechanism may enable us to understand and improve the efficiency of the reaction. This review covers the mechanistic aspects, studied both from theoretical and experimental points of view, of the transition-metal-catalyzed [2 + 2 + 2] cycloaddition reaction involving all kinds of unsaturated substrates with metals such as Co, Ni, Ru, Rh, Ir, Pd, Zr, Ti, Ta, and Nb. A thorough overview is undertaken, from the seminal studies until the present day, of the key mechanistic aspects that influence the reactivity and selectivity of the reaction, comparing the involvement of different unsaturated substrates as well as the different transition metals used.
    Language English
    Publishing date 2020-07-30
    Publishing country United States
    Document type Journal Article ; Research Support, Non-U.S. Gov't
    ZDB-ID 207949-5
    ISSN 1520-6890 ; 0009-2665
    ISSN (online) 1520-6890
    ISSN 0009-2665
    DOI 10.1021/acs.chemrev.0c00062
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    Z 4' 49/78: Show issues
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