All posts by administrador

J. Org. Chem. 12.2019

Synthesis and Photophysical Behavior of a Highly Fluorescent Family of Unsymmetrical Organoboron Complexes Containing 5-(Pyridin-2-ylmethylene)imidazolidine-2,4-dione Moieties

M. Soledad Garre, Raúl Losantos, Sara Gutiérrez, David Sucunza, Patricia García-García, Diego Sampedro and Juan J. Vaquero

J. Org. Chem., Article ASAP
DOI: 10.1021/acs.joc.9b02451

A new and highly fluorescent family of unsymmetrical organoboron complexes containing 5-(pyridin-2-ylmethylene)imidazolidine-2,4-dione moieties has been synthesized in three steps. These compounds show strong absorptions covering a wide range of the UV–vis spectrum and are strongly emissive (ϕf of up to 0.92 in CH3CN). Moreover, two fluorophores that include an alkyne or an azide group at the end of the alkyl chain and with potential utility in bioorthogonal chemistry have been developed. One of these, in which the glycol substituent provides an enhanced water solubility without compromising the fluorescence (ϕf = 0.85 in water), may be of particular importance.

Rubén Manzano

Rubén Manzano San José

Assistant Professor

    • Associated Professor, Universidad de Valladolid (2022)
    • Assistant Professor, Universidad de Alcalá (2019-2022)
    • Postdoctoral researcher, Prof. J. L. Vicario group, Universidad del País Vasco (2017-2019)
    • Marie-Curie Fellowship, Prof. D. J. Dixon group, Universidad de Oxford (2015-2017)
    • Postdoctoral researcher ICIQ-IPMP, Prof. R. Martín group, ICIQ (2013-2015)
    • Postdoctoral researcher, Prof. A. S. K. Hashmi group, CaRLa-Universidad de Heidelberg (2011-2013)
    • Ph.D. Universidad de Valladolid (2010), supervisors Prof. R. Pedrosa and Prof. J. M. Andrés
    • Graduated at the Universidad de Valladolid (2005)

    I developed my PhD Thesis at the Universidad de Valladolid on the synthesis of chiral thioureas derived from amino acids and their applications as organocatalysts in enantioselective reactions of interest. Later, as postdoctoral researcher in the groups of Prof. A. S. K. Hashmi and Prof. R. Martín, I developed synthetic methodologies with gold, ruthenium, nickel and palladium catalysis. I then obtained a prestigious Marie-Curie Fellowship to carry out a project of dual enantioselective catalysis (aminocatalysis and metal catalysis with silver and copper) in the laboratories of Prof. D. J. Dixon at Oxford University. After this stage, I joined Prof. J. L. Vicario’s group at the Universidad del País Vasco as a contracted researcher, where I worked on the discovery of new reactivity patterns by enantioselective catalysis by phosphoric acids and by chiral phosphines, as well as on the synthesis of natural products. In October 2019 I joined the Universidad de Alcalá as Assistant Professor. The results of my research are collected in twenty publications, most of them with a high impact rate (ACIE (3), JACS (2), CEJ (3)…). During my research career I have supervised many students during the completion of their Master thesis and Bachelor thesis, as well as during external internships.

  • Clara Mañas

    Clara Mañas

    • Project associate researcher (2024)
    • Thesis defense, 04.03.2024 (“Design and study of novel reactivities of alkynylazobenzenes”)
    • Project associate researcher. Department of Organic and Inorganic Chemistry
    • Master Organic Synthesis Universidad Autónoma de Madrid (2018/2019)
    • Graduated at the Universidad Complutense de Madrid (2014-2018)

    Publicaciones en el grupo

    Copper-Catalyzed Hydroamination of 2-Alkynylazobenzenes: Synthesis of 3-Alkenyl-2H-Indazoles.
    J Org Chem. 2024 Nov 15;89(22):16883-16888. doi: 10.1021/acs.joc.4c02144. Epub 2024 Nov 2.
    Combined Gold and Photoredox Catalysis: Synthesis of 3-Alkenyl-2H-Indazoles from 2-Alkynylazobenzenes.
    Advanced Synthesis & Catalysis. 2025; 367(1):e202400990.
    Visible Light-Mediated Heterodifunctionalization of Alkynylazobenzenes for 2H-Indazole Synthesis.
    Org Lett. 2024, 26, 1868
    Electrochemically driven one-pot oxidative conversion of arylhydrazines into aromatic iodides.
    J. Environ. Chem. Eng. 2022, 10, 107486

    Julia Altarejos

    Julia Altarejos

    • Thermo Fisher Scientific 04.2024
    • Postdoctoral Researcher (2023-2024)
    • Thesis defense, 22.09.2023 (“Estudio de la reactividad del 2,2,2-trifluorodiazoetano en la síntesis de ciclopropanos y pirazoles y en la funcionalización de alcanos”)
    • Predoctoral stay, Prof. John F. Hartwig (University of California, Berkeley)
    • FPU grant Ministerio de Educación y Formación Profesional 2019-2023
    • Master Drug Discovery Universidad de Alcalá (2018/2019)
    • Graduated at the Universidad de Jaén (2014-2018)

    Publications in the group

    Alkanes C(1)-C(6) C-H Bond Activation via a Barrierless Potential Energy Path: Trifluoromethyl Carbenes Enhance Primary C-H Bond Functionalization.
    J Am Chem Soc. 2024 Dec 11;146(49):34014-34022. doi: 10.1021/jacs.4c13065. Epub 2024 Nov 25.
    One-Pot (3 + 2) Cycloaddition-Isomerization-Oxidation of 2,2,2-Trifluorodiazoethane and Styryl Derivatives.
    J Org Chem. 2023, 88, 11258
    Synthesis of Tri- and Tetrasubstituted Alkenyl Boronates from Alkynes.
    Eur. J. Chem. 2022, e202200521.
    Enantioselective Copper-Catalyzed Synthesis of Trifluoromethyl-Cyclopropylboronates.
    Org Lett. 2021 Aug 6;23(15):6174-6178. doi: 10.1021/acs.orglett.1c02420.
    Practical Solvent-Free Microwave-Assisted Hydroboration of Alkynes.
    Eur. J. Org. Chem. 2020, 3024

    UK-Spain Organometallic Chemistry Symposium

    UK-Spain Organometallic Chemistry Symposium (USOCS2019)

     

    UK-Spain Organometallic Chemistry Symposium (USOCS2019),  Alcalá de Henares, September 17-19th:

    · BN-Arenes: Synthesis, Reactivity and Properties
    Alberto Abéngozar, Isabel Valencia, Miguel Ángel Fernández, Luis Manuel Frutos, Antonio Salgado, Adrián Pérez Redondo, Patricia García-García, David Sucunza, Juan J. Vaquero

    · Decarbonylation Processes in k3 -(N^C^C) Gold (III) Carboxylates
    Estíbaliz Merino, Hélène Beucher, Alexandre Genoux, Thomas Fox, Cristina Nevado

    · Gold-catalyzed regiodivergent cyclization of alkynylcyclobutanes
    M. Soledad Garre, David Sucunza, Estíbaliz Merino, Enrique Agular, Patricia García-García, Juan J. Vaquero

    · Stereoselective synthesis of versatile trifluoromethyl substituted borocyclopropanes
    Julia Altarejos, David Sucunza, Ana Caballero, Pedro J. Pérez, Juan J. Vaquero, Javier Carreras

    International Symposium on Advances in Synthetic and Medicinal Chemistry

    EFMC-ASMC19 (International Symposium on Advances in Synthetic and Medicinal Chemistry) and ASMC-YSMC (6th EFMC Young Medicinal Chemist Symposium)

     

    INTO THE ILK-αPARVIN INTERACTION AS A NEW STRATEGY AGAINST CHRONIC KIDNEY DISEASE
    García Marín, Javier; De Frutos, Sergio; Griera, Mercedes; Alajarín Ferrandez, Ramón; Griera Merino, Mercedes; Vaquero López, Juan J.; Rodriguez Puyol, Diego; Rodriguez Puyol, Manuel

    · International Symposium on Advances in Synthetic and Medicinal Chemistry, September 1-5th, Athens
    · 6th EFMC Young Medicinal Chemist Symposium, September 5-6th, Athens

    Almirall prize SEQT – Javier García Marín

    Almirall prize SEQT – Javier García Marín

    Javier García Marín won Almirall prize of Sociedad Española de Química Terapéutica (SEQT) para Investigadores Noveles en el Campo de la Búsqueda y desarrollo de Nuevos Fármacos. Congratulations!

    The award was received during the 19th Meeting of the Spanish Society of Medicinal Chemistry, Vitoria.
    Flash communication:
    New tools in medicinal chemistry: design, synthesis & evaluation of new molecules for the modulation of integrin linked kinase: a new target for chronic kidney disease.

    Master’s Thesis “Drug Discovery” 2019

    Master’s Thesis “Drug Discovery” 2019

    School of Drug Discovery of the Interuniversity Master’s Degree in Drug Discovery

    In this edition, five works tutored in the group have been presented. Congratulations!

    • Julia Altarejos “Síntesis estereoselectiva de trifluorometilciclopropilboronatos”
    • Paula Flores “Síntesis de compuestos policíclicos mediante ciclaciones electrofílicas de eninos”
    • Miriam Ramírez “Synthesis of small molecules as mimetics of the epitope segment in ILK-a-parvin protein-protein interaction”
    • Alexey Sanduev “Design and synthesis of dicationic cromophores with application in bioimaging”
    • Silvia Simón “Synthesis of modulators of integrin-linked kinase (ILK)”