Archivo de la categoría: Publicación

2023, Publicación

Zurro et al. Synthesis 2023: Visible-Light-Mediated Regioselective Chlorosulfonylation of Acrylamides.

Publicaciones > Zurro et al

Synthesis 2023, DOI: 10.1055/s-0042-1751424.

Visible-Light-Mediated Regioselective Chlorosulfonylation of Acrylamides.

Mercedes Zurro, Sergio Torres-Oya, Guillermo G. Otárola, Juan José Vaquero, Estíbaliz Merino

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.

2023, Au, Publicación

Garre et al. Org Biomol Chem. 2023;21(13):2705-2708. Gold-catalyzed endo-selective cyclization of alkynylcyclobutanecarboxamides: synthesis of cyclobutane-fused dihydropyridones.

Publicaciones > Garre et al

Org Biomol Chem. 2023 Mar 29,21,2705-2708. doi: 10.1039/d3ob00051f. PubMed 36919647

Gold-catalyzed endo-selective cyclization of alkynylcyclobutanecarboxamides: synthesis of cyclobutane-fused dihydropyridones.

M Soledad Garre1, a, Guillermo G Otárola1, b, Estíbaliz Merino1, c, David Sucunza1, d, Enrique Aguilar2, M Teresa Quirós1, e, Juan J Vaquero1, f, Patricia García-García1, g

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.

2023, AzaBN, Publicación

Valencia et al. Synthesis 2023. Synthesis of Five-Membered Organoborate Heterocycles via a Metal-Free Carboboration and Their Use in Cross-Coupling Reactions.

Publicaciones > Valencia et al

Synthesis 2023, 55, 1260-1266. doi: 10.1055/a-1979-6009

Synthesis of Five-Membered Organoborate Heterocycles via a Metal-Free Carboboration and Their Use in Cross-Coupling Reactions.

Isabel Valencia, David Sucunza, Patricia García-García, Adrián Pérez-Redondo, Juan J. Vaquero

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.