XIV Spanish-Italian Symposium on Organic Chemistry
Torino, Italy, 25 – 27 February 2024
· Heterodifunctionalization of Alkynes Promoted Exclusively by Visible Light
Clara Mañas, Estíbaliz Merino
Flash communication
SISOC-XIV participation
All posts by administrador
Milián et al. Advanced Synthesis & Catalysis. 2024;366(2):232 -240. Title
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Palabras clave: Cyclization; Gold; Laetevirenol A; Substituent effects; Total synthesis
Resumen
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Hervieu et al. Nat Chem. 2024;:. Chiral arylsulfinylamides as reagents for visible light-mediated asymmetric alkene aminoarylations.
Chiral arylsulfinylamides as reagents for visible light-mediated asymmetric alkene aminoarylations.
1. Department of Chemistry, University of Zurich, Zurich, Switzerland. 2. Universidad de Alcalá, Departamento de Química Orgánica y Química Inorgánica, Instituto de Investigación Andrés M. del Río (IQAR), Facultad de Farmacia, Madrid, Spain. 3. Instituto Ramón y Cajal de Investigación Sanitaria (IRYCIS), Madrid, Spain.
a. estibaliz.merino@uah.es b. estibaliz.merino@uah.es
Abstract
Two- or one-electron-mediated difunctionalizations of internal alkenes represent straightforward approaches to assemble molecular complexity by the simultaneous formation of two contiguous Csp(3) stereocentres. Although racemic versions have been extensively explored, asymmetric variants, especially those involving open-shell C-centred radical species, are much more limited both in number and scope. Here we describe enantioenriched arylsulfinylamides as all-in-one reagents for the efficient asymmetric, intermolecular aminoarylation of alkenes. Under mild photoredox conditions, nitrogen addition of the arylsulfinylamide onto the double bond, followed by 1,4-translocation of the aromatic ring, produce, in a single operation, the corresponding aminoarylation adducts in enantiomerically enriched form. The sulfinyl group acts here as a traceless chiral auxiliary, as it is eliminated in situ under the mild reaction conditions. Optically pure β,β-diarylethylamines, aryl-α,β-ethylenediamines and α-aryl-β-aminoalcohols, prominent motifs in pharmaceuticals, bioactive natural products and ligands for transition metals, are thereby accessible with excellent levels of regio-, relative and absolute stereocontrol.
Martín Romero
Rafael Martín Romero Segura
Assistant Professor
orcid.org/0000-0003-3218-8661- 2023-present: Assistant Professor at Universidad de Alcalá (UAH) (Madrid).
- 2022-2023: «Maria Zambrano» Postdoctoral Research Fellow at Universidad Autónoma de Madrid (UAM) (Madrid) (Prof. M. Tortosa).
- 2019-2021: Postdoctoral researcher at Commissariat à l’énergie atomique et aux énergies alternatives (CEA) (France) (Prof. T. Cantat group).
- 2018-2019: Postdoctoral researcher-Oril Industries (Servier Group), École Nationale Supérieure de Chimie de Montpellier (ENSCM) (France) (Prof. M. Taillefer).
- 2017: PhD (FPU) at Universidad Rovira I Virgili (URV) / Institut Català d’Investigació Química (ICIQ), (Prof. K. Muñiz) Development of hypervalent iodine(III)-mediated chemical reactions.
- 2015: Predoctoral internship student at University of Michigan (USA) (Prof. J. P. Wolfe).
- 2012: Master in Biotechnology at Universidad de Málaga (UMA) / Universidad Internacional de Andalucía (UNIA).
- 2011: Graduated (Chemistry) at Universidad de Málaga.
- 2010: JAE-Intro Summer Research Fellow at Universidad Complutense de Madrid / Instituto de Química Orgánica General (Prof. P. Almendros).
Dr. Carreras promoted to Associate Professor at the UAH
Dr. Carreras promoted to Associate Professor at the UAH
Last Tuesday, December 12, Dr. Javier Carreras successfully passed hir exam and was appointed as Associate Professor at the UAH.
Congratulations Javi!
Maqueda-Zelaya et al. The Journal of Organic Chemistry. 2023;88(19):14131 -14139. 1,2,3-Benzotriazine Synthesis by Heterocyclization of p-Tosylmethyl Isocyanide Derivatives.
Publications > Maqueda-Zelaya et al
1,2,3-Benzotriazine Synthesis by Heterocyclization of p-Tosylmethyl Isocyanide Derivatives.
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Patricia García – junior director’s award in science branches 2023
Dr. Patricia García has received the award for junior director in the area of science, health sciences, engineering and architecture in the 2023 call.
This award is a recognition of the work done by the faculty of the University of Alcalá for obtaining results in the field of research training.
Congratulations!
J. Org. Chem. 09.23
1,2,3-Benzotriazine Synthesis by Heterocyclization of p-Tosylmethyl Isocyanide Derivatives
Francisco Maqueda-Zelaya, José Luis Aceña*, Estíbaliz Merino, Juan J. Vaquero, and David Sucunza*
J. Org. Chem. 2023, ASAP
DOI: 10.1021/acs.joc.3c01675
| An efficient methodology to form 4-alkoxy- and 4-aryloxybenzo[d][1,2,3]triazines via an intramolecular heterocyclization of 1-azido-2-[isocyano(p-tosyl)methyl]benzenes under basic conditions has been developed. DFT calculations have been performed to further understand the mechanism of this heterocyclization, which occurs in good to excellent yields with a broad scope. |
XXV EuCOMC participation
XXV EuCOMC, XXV CONFERENCE ON ORGANOMETALLIC CHEMISTRY
Alcalá de Henares, 4 – 8 septembre
– Póster:
· Copper-catalyzed intramolecular cyclization of alkynylazobenzenes for the synthesis of 2H-indazoles
Clara Mañas, Juan Herrero, Estíbaliz Merino
– Póster:
· Visible-Light-Mediated Regioselective Chlorosulfonylation of Acrylamides
Guillermo G. Otárola, Mercedes Zurro, Sergio Torres-Oya, Juan José Vaquero, Estíbaliz Merino
– Póster:
· Direct conversion of C1−C6 alkanes into trifluoromethyl derivatives
Jonathan Martínez-Laguna, M. Ángeles Fuentes, Julia Altarejos, Javier Carreras, Ana Caballero, Pedro J. Pérez
Zurro et al. European Journal of Organic Chemistry. 2023;n/a(n/a):e202300535. Visible-light mediated synthesis of bicalutamide by regioselective hydroxysulfonylation of acrylamides.
Visible-light mediated synthesis of bicalutamide by regioselective hydroxysulfonylation of acrylamides.
Palabras clave: Bicalutamide; acrylamides; difunctionalization of alkenes; α-hydroxysulfones; hydroxysulfonylation
Resumen
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