Archivo de la categoría: Noticias

Participación XVIII SJIQ

XVIII Simposio de Jóvenes Investigadores Químicos de la RSEQ

Sevilla, 21 – 28 noviembre

– 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



Nuevo artículo, Synthesis 11.22

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 Vaquero López

Synthesis 2022, Accepted Articles
DOI: 10.1055/a-1979-6009

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.

Nuevo artículo, Adv. Synth. Catal. 10.22

Synthesis of Phenanthrene-based Polycycles by Gold(I)-Catalyzed Cyclization of Biphenyl-Embedded Trienynes

Ana Milián, Patricia García-García,* Juan J. Vaquero, Roberto Sanz, Manuel Ángel Fernández-Rodríguez*

Adv. Synth. Catal. 2022, Accepted Articles
DOI: 10.1002/adsc.202200887

Gold(I)-catalyzed cyclization of o-alkenyl-o’-alkynylbiaryls in the presence of external or internal nucleophiles provides a straightforward access to phenanthrene-based polycycles, which are of considerable interest in materials science. Thus, their reactions with alcohols yield functionalized dihydrophenanthrenes, in a process that can also be carried out intramolecularly to provide phenanthrene-derived heteropolycyclic compounds. Moreover, benzo[b]triphenylenes can be synthesized from o-methoxyvinyl-o’-alkynylbiaryls, in a reaction in which an (hetero)aryl substituent at the triple bond acts as an internal nucleophile.

Nuevo artículo, Dyes and Pigments 08.22

Highly efficient unbridged D-A+(D) chromophores based on the quinolizinium cation for nonlinear optical (NLO) applications

Esmeralda Sánchez-Pavón, Javier Recio, Marco Antonio Ramirez, Belen Batanero, Koen Clays, Francisco Mendicuti, Gema Marcelo, Thais Carmona, Obis Castaño, Silvia Angelova, Jose L. Andres, Juan J. Vaquero, Ana M. Cuadro*

Dyes and Pigments 2022, ASAP
DOI: 10.1016/j.dyepig.2022.110323

Novel charged D-A+ chromophores based on quinolizinium cations as acceptor unit have been prepared by treating haloquinolizinium salts with N-heteroarylstannanes under Stille reaction conditions. This approach provides an easy access to potential one-dimensional D-A+ and two-dimensional D-A+-D chromophores in which the acceptor moiety (A+) is the simple azonia cation and the donors are different π-rich N-heterocycles. The first hyperpolarizabilities (β) were measured by hyper-Rayleigh scattering experiments and the experimental data confirmed that the inherent polarization between donor and acceptor fragments modulates the NLO properties. The electronic structures and properties (including both the linear and nonlinear optical properties) of the quinolizinium chromophores were examined by theoretical (DFT, HF and MP2) calculations. A promising strategy for the rational design of D-A building blocks to create new organic-based NLO materials is proposed..

Nuevo artículo, Org.Lett 08.22

Synthesis of BN-Polyarenes by a Mild Borylative Cyclization Cascade

Ester Sans-Panadés, Juan J. Vaquero, Manuel A. Fernández-Rodríguez*, Patricia García-García*

Org. Lett. 2022, ASAP
DOI: 10.1021/acs.orglett.2c02477

Reaction of BCl3 with suitably substituted o-alkynylanilines promotes a cascade reaction in which BN-polycyclic compounds are obtained via the formation of two new cycles and three new bonds in a single operational step. The reaction is highly efficient and takes place at room temperature, providing a very mild and straightforward strategy for the preparation of BN-aromatic compounds, which can be further transformed into a variety of BN-PAHs with different polycyclic cores and substituents.

Nuevo artículo, EurJOC 07.22

Synthesis of Tri- and Tetrasubstituted Alkenyl Boronates from Alkynes

Julia Altarejos, Antonio Valero, Rubén Manzano,* Javier Carreras*

Eur. J. Org. Chem. 2022, #NextGenOrgChem
DOI: 10.1002/ejoc.202200521

The synthesis of organoboron compounds have attracted the attention of the synthetic community. In particular, molecules with C(sp2)-B bonds enable the transformation to new C−C or C-heteroatom bonds by well-established methodologies. Alkenyl boronates have the possibility for further conversion of the boron moiety or functionalization of the double bond. This review gives an overview on the recent methodologies for the selective preparation of the challenging highly substituted alkenyl boronates from alkynes.

Participación congresos

22nd Tetrahedron Symposium

Lisbon, 28 June – 1 July

– Póster:
· Photocatalytic synthesis of indazoles from alkynylazobenzenes
Clara Mañas, Estíbaliz Merino

– Póster:
· Metal-free synthesis of medium-sized rings by cationic carbocyclization of trienynes
Jaime Tostado Sánchez, Ana Milián, Juan J. Vaquero, Manuel A. Fernández-Rodríguez

XXXVIII Reunión Bienal de la Real Sociedad Española de Química (RSEQ)

Granada, 27-30 June

– Oral:
· Asymmetric Photocatalysis Through Smiles Rearrangements
Estíbaliz Merino

– Oral:
· Drogas, fármacos y venenos: el impacto de los productos naturales en la historia
David Sucunza

– Póster:
· Progress towards the synthesis of Laetevirenol A
Lucía Sánchez Jiménez, Ana Milián, Jaime Tostado, Juan J. Vaquero, Patricia García García, Manuel A. Fernández Rodríguez

– Póster:
· Gold(I) catalyzed cyclization of alkynylcyclobutanamides towards lactams
Guillermo G. Otárola, María Soledad Garre, Estíbaliz Merino, David Sucunza, Juan J. Vaquero, Patricia García-García

– Póster:
· Catalytic (enantioselective) access to 4-(sec-alkyl)anilines via 1,6-conjugate addition of Grignard reagents to in situ generated aza-p-quinone methides
Mercedes Zurro, L. Ge, S. R. Harutyunyan

XXVIII REUNIÓN BIENAL del Grupo Especializado de Química Orgánica

Granada, 1 July

– Póster:
· Photocatalytic synthesis of a-chloro- and a-hydroxy b-sulfonylamides. Preparation of anticancer drug Bicalutamide
Sergio Torres, Mercedes Zurro, Estíbaliz Merino

– Póster:
· Preparation of 5-aryl-3-trifluoromethylpyrazoles: one-pot metal-free transformation from styrenes and 2,2,2-trifluorodiazoethane
Julia Altarejos, David Sucunza, Juan José Vaquero, Estíbaliz Merino, Javier Carreras

Introducing… Patricia en Angew Chem

Introducing… Patricia en Angew Chem

Patricia García-García ha publicado su primer Angewandte Chemie como autora de correspondencia:

Metal-Free Temperature-Controlled Regiodivergent Borylative Cyclizations of Enynes: BCl3-Promoted Skeletal Rearrangement: A. Milián, M. A. Fernández-Rodríguez, E. Merino, J. J. Vaquero, P. García-García, Angew. Chem. Int. Ed. 2022, doi.org/10.1002/anie.202205651.

https://onlinelibrary.wiley.com/doi/10.1002/anie.202207530

Nuevo artículo, Angew. Chem. Int. Ed. 05.22

Metal-Free Temperature-Controlled Regiodivergent Borylative Cyclizations of Enynes: BCl3-Promoted Skeletal Rearrangement

Ana Milián, Manuel A. Fernández-Rodríguez,* Estíbaliz Merino, Juan J. Vaquero, Patricia García-García*

Angew. Chem. Int. Ed. 2022, Accepted Articles
DOI: 10.1002/anie.202205651

Metal-free borylative cyclization of biphenyl-embedded 1,3,5-trien-7-ynes in the presence of simple and inexpensive BCl3 provided synthetically useful borylated building blocks. The outcome of the process depends on the reaction temperature, with borylated phenanthrenes obtained at 60 ºC and phenanthrene-fused borylated cyclobutanes formed at 0 ºC. Based on DFT calculations, a mechanism for these novel transformations has been proposed, which involves an uncommon skeletal rearrangement, including migration of a methyl group and alkyne fragmentation, unprecedented in BCl3-promoted cyclization reactions.