β-Functionalization of 4 a-aza-8 a-boranaphthalene via Iridium-catalyzed C−H Borylation.
Palabras clave: BN-naphthalene; C−H activation; iridium; cross-coupling; catalysis
Resumen
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ACS Macro Lett. 06.2023
Hyper-Cross-Linked Porous Polymer Featuring B–N Covalent Bonds (HCP-BNs): A Stable and Efficient Metal-Free Heterogeneous Photocatalyst
Sara Señorans, Isabel Valencia, Estíbaliz Merino, Marta Iglesias, Manuel A. Fernández-Rodríguez*, Eva M. Maya*
ACS Macro Lett. 2023, ASAP
DOI: 10.1021/acsmacrolett.3c00217
| The first example of a porous polymer containing B–N covalent bonds, prepared from a tetraphene B–N monomer and biphenyl as a comonomer, is reported. It was prepared using the solvent knitting strategy, which allows the connection between the aromatic rings of the two monomers through methylene groups provided by an external cross-linking agent. The new polymer exhibited micromeso porosity with an SBET of 612 m2/g, high thermal stability, and potential properties as a heterogeneous photocatalyst, since it is very active in the aza-Henry coupling reaction (>98% of conversion and selectivity). After the first run, the catalyst improves its photocatalytic activity, shortening the reaction time to only 2 h and maintaining this activity in successive runs. The presence of a radical in this structure that remains stable with successive runs makes it a new type of material with potential applications as a highly stable and efficient photocatalyst. |
Dra. Rosa López talk, 14.06.23
Dra. Rosa López Álvarez
Dra. Rosa López Álvarez, Senior Researcher, Universidad del País Vasco (Campus de San Sebastián)
Challenges in Brønsted Base Catalysis: An Opportunity for Structure Design
Sala de Grados, Edificio de Farmacia, UAH. June 14th, 12.00.
ChemSusChem 05.23
Mizoroki–Heck Macrocyclization Reactions at 1 M Concentration Catalyzed by Sub-nanometric Palladium Clusters
Francisco Garnes–Portolés, Estíbaliz Merino, Antonio Leyva–Pérez*
ChemSusChem 2023, Accepted Articles
DOI: 10.1002/cssc.202300200
| Mizoroki-Heck macrocyclization reactions are carried out at 1M concentration with ligand-free Pd cluster catalysts either in solution or supported on solids. Mechanistic studies unveil the essential role of the fluxional Pd cluster to accommodate, at the same time, the reacting groups, to give the intramolecular vs the intermolecular coupling reaction at this high concentration, enabling (in-flow) solid-catalyzed macrocyclization reactions. |
Garnes-Portolés et al. ChemSusChem. 2023;n/a(n/a):e202300200. Mizoroki-Heck Macrocyclization Reactions at 1 M Concentration Catalyzed by Sub-nanometric Palladium Clusters.
Publications > Garnes-Portolés et al
Mizoroki-Heck Macrocyclization Reactions at 1 M Concentration Catalyzed by Sub-nanometric Palladium Clusters.
Palabras clave: macrocyclization; high concentration; Mizoroki-Heck reaction; Pd clusters; solid catalysts
Resumen
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Zurro et al. Journal. 2023;(EFirst):. Visible-Light-Mediated Regioselective Chlorosulfonylation of Acrylamides.
Visible-Light-Mediated Regioselective Chlorosulfonylation of Acrylamides.
Palabras clave: acrylamides; difunctionalization of alkenes; photocatalysis; chlorosulfonylation; α-chlorosulfones
Resumen
A one-step chlorosulfonylation of acrylamides via a photocatalytic redox process is described. This reaction provides α-chlorosulfonylamides with a quaternary center with high regioselectivity via radical process. It is amenable to a broad range of substrates and the products are obtained in moderate to good yields.
Garre et al. Org Biomol Chem. 2023;21(13):2705-2708. Gold-catalyzed endo-selective cyclization of alkynylcyclobutanecarboxamides: synthesis of cyclobutane-fused dihydropyridones.
Gold-catalyzed endo-selective cyclization of alkynylcyclobutanecarboxamides: synthesis of cyclobutane-fused dihydropyridones.
1. Universidad de Alcalá (IRYCIS), Departamento de Química Orgánica y Química Inorgánica, Instituto de Investigación Química "Andrés M. del Río" (IQAR), Campus Científico-Tecnológico, Facultad de Farmacia, Autovía A-II, Km 33.1, 28805-Alcalá de Henares, Madrid, Spain. 2. Departamento de Química Orgánica e Inorgánica, Instituto Universitario de Química Organometálica "Enrique Moles", Universidad de Oviedo, C/Julián Clavería, 8, 33006 Oviedo, Spain.
a. juanjose.vaquero@uah.es b. juanjose.vaquero@uah.es c. juanjose.vaquero@uah.es d. juanjose.vaquero@uah.es e. juanjose.vaquero@uah.es f. juanjose.vaquero@uah.es g. juanjose.vaquero@uah.es
Abstract
Cyclobutane-fused dihydropyridones can be efficiently synthesized by a completely endo-selective gold-catalyzed cyclization of alkynylcyclobutanes bearing an appended amide, which proceeds under mild conditions. The observed selectivity, which is reversed from that previously observed for the cyclization of related alcohols and acids, is supported by DFT calculations.
Synthesis 03.23
Visible-Light-Mediated Regioselective Chlorosulfonylation of Acrylamides
Mercedes Zurro, Sergio Torres-Oya, Guillermo G. Otárola, Juan José Vaquero, Estíbaliz Merino*
Synthesis 2023, Special Issue dedicated to Prof. Cristina Nevado, recipient of the 2021 Dr. Margaret Faul Women in Chemistry Award
DOI: 10.1055/s-0042-1751424
| A one-step chlorosulfonylation of acrylamides via a photocatalytic redox process is described. This reaction provides α-chlorosulfonylamides with a quaternary center with high regioselectivity via radical process. It is amenable to a broad range of substrates and the products are obtained in moderate to good yields. |
Org. Biomol. Chem. 03.23
Gold-catalyzed endo-selective cyclization of alkynylcyclobutanecarboxamides: synthesis of cyclobutane-fused dihydropyridones
M. Soledad Garre, Guillermo G. Otárola, Estíbaliz Merino, David Sucunza, Enrique Aguilar, M. Teresa Quirós, Juan J. Vaquero* and Patricia García-García*
Org. Biomol. Chem. 2023, Advance Article
DOI: 10.1039/D3OB00051F
| Cyclobutane-fused dihydropyridones can be efficiently synthesized by a completely endo-selective gold-catalyzed cyclization of alkynylcyclobutanes bearing an appended amide, which proceeds under mild conditions. The observed selectivity, which is reversed from that previously observed for the cyclization of related alcohols and acids, is supported by DFT calculations. |
Valencia et al. Journal. 2023;(EFirst):. Synthesis of Five-Membered Organoborate Heterocycles via a Metal-Free Carboboration and Their Use in Cross-Coupling Reactions.
Synthesis of Five-Membered Organoborate Heterocycles via a Metal-Free Carboboration and Their Use in Cross-Coupling Reactions.
Palabras clave: metal-free carboboration; organoboron compounds; organoborate heterocycles; cross-coupling reactions; boron chemistry
Resumen
Treatment of various vinylbenzopyridines with allyl(dichloro)borane affords five-membered organoborate heterocycles via a metal-free carboboration. The reaction between these organoborates and Grignard reagents increases the number of derivatives belonging to this novel family of four-coordinate organoboron compounds. Some of them were used as reagents in phenylations and methylations in moderate to high yields under standard palladium-catalyzed cross-coupling reaction conditions.