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.
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. |
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
No hay resumen
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.
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.
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. |
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. |
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.
Sevilla, 21 – 28 November
– Oral:
· Metal-free synthesis of 3-trifluoromethypyrazoles: [3+2] cyclization of styrenes and 2,2,2-trifluorodiazoethane
Julia Altarejos, David Sucunza, Juan J. Vaquero, Estíbaliz Merino, and Javier Carreras
– Póster:
· Visible-light mediated synthesis of indazoles
Clara Mañas, Estíbaliz Merino
– Póster:
· Synthesis of novel five membered organoborate heterocycles and their use in cross-coupling reactions
Isabel Valencia, Patricia Garcia-Garcia, David Sucunza, Adrián Pérez-Redondo, Juan J. Vaquero
orcid.org/0000-0002-7953-4798.