Dr. Ana Belen Cuenca, Full Professor, Organic & Pharmaceutical Chemistry Department (Universitat Ramon Llul).
New reactions and structures involving main group elements
Sala de Grados, School of Pharmacy, UAH. May 23rd, 12.30.
Dr. Carlos Vila Descals, Associate professor, Organic Chemistry Department (Universidad de Valencia).
Stereoselective functionalization of nitrogen heterocycles using metal catalysis, organocatalysis or photocatalysis
Sala de Grados, School of Pharmacy, UAH. May 23rd, 12.30.
Guillermo Morales-Ortega, Estíbaliz Merino and Javier Carreras*
We report a simple protocol for the transformation of Csp3–Csp3 to Csp3–N in homobenzylic sulfonamides in combination with N-iodoimides to form gem-diamino derivatives. The reaction exhibits a wide functional group tolerance and allows the incorporation of bioactive-derived fragments. The mechanistic insights provided by control experiments and DFT calculations suggest that an imine intermediate is formed after C−C bond cleavage.
Chem. Sci. 2025
DOI: 10.1039/D5SC02168E
Marcos Humanes, Manuel A. Fernández-Rodríguez,* Patricia García-García*
A selective, metal-free method for the synthesis of boron-functionalized polysubstituted naphthalenes via BCl3-mediated cyclization of α-substituted o-alkynylstyrenes is described. The reaction exhibits broad substrate scope, tolerating various groups such as ethers, sulfides and halogens, and delivers high yields under mild conditions, even at gram scale. The resulting Bpin-functionalized naphthalenes serve as versatile building blocks, facilitating further transformations of the C−B bond into C−H, C−C, C−I, C−O, and C−N bonds, thereby increasing molecular complexity and enabling the design of more functionalized products. Notably, this sustainable and straightforward protocol selectively introduces the Bpin group at the sterically hindered α-carbon of the naphthalene framework, complementing C–H borylations of the naphthalene core, that preferentially occur at the β-position. As a result, the developed approach significantly broadens the accessibility of B-functionalized naphthalene derivatives for synthetic and application-oriented purposes.
Adv. Synth. Cat. 2025
DOI: 10.1002/adsc.202500244
Dr. Francisco Juliá-Hernández, Ramon y Cajal Fellow, Inorganic Chemistry Department (Universidad de Murcia).
Illuminating Earth-abundant Metals: New Opportunities in Organic Synthesis
Sala de Grados, School of Pharmacy, UAH. April 25th, 12.30.
Our two young members Guillermo Sánchez Mateos and Erica Salivioli have been awarded with a FPI-UAH contract to carry out their doctoral thesis at the UAH.
Congratulations 😊!
Marta Durán, Juan José Vaquero, Mercedes Griera, Sergio de Frutos, Diego Rodríguez Puyol, Javier García Marín*
La presente invención se refiere a nuevos compuestos que actúan como ligandos de la quinasa ligada a integrinas (del inglés ILK), facilitando la polimerización del citoesqueleto de actina y favoreciendo así el tráfico de receptores celulares desde los compartimentos intracelulares a la superficie de las células. Por este motivo, pueden ser utilizados en enfermedades como la diabetes mellitus tipo 2 o la diabetes insípida nefrogénica y, por extensión, en cualquier enfermedad en la que las alteraciones fisiopatológicas sean debidas, total o parcialmente, a un transporte transmembrana disminuido como las tubulopatías renales originadas por una pérdida de transportadores.
No: P202530222 (14/03/2025)
Clara Mañas, Estíbaliz Merino*
We disclose the intramolecular synthesis of 3-alkenyl-2H-indazoles from 2-alkynylazobenzenes, promoted by a dual catalysis using AuCl3 and a ruthenium photocatalyst under visible light irradiation. This reaction proceeds through hydroamination of the alkynyl fragment. The yields are influenced by electronic factors. Control experiments suggest that both radical and polar mechanisms operate in parallel. This transformation involves C−N bond formation and a 1,2-hydride shift. Additionally, derivatization was performed to demonstrate the versatility of this methodology..
Adv. Synth. Cat. 2025
DOI: 10.1002/adsc.202400990
Clara Mañas, Juan Herrero-Bordieu, Estíbaliz Merino*
A copper-catalyzed intramolecular synthesis of 3-alkenyl-2H-indazoles from 2-alkynylazobenzenes is described. The reaction proceeds in a single step via C–N bond formation and a subsequent 1,2-hydride shift, affording products in high yields. DFT calculations suggest the 1,2-hydride shift as the rate-determining step. Further derivatization enables functionalization of the 3-alkenyl-2H-indazoles.
J. Org. Chem. 2024
DOI: 10.1038/10.1021/acs.joc.4c02144
Clara Mañas, Belén Ibarra, Estíbaliz Merino*
The development of regiodivergent methods that allow access to different structures from a single substrate through intramolecular processes is crucial for accelerating new molecule discovery, as well as making processes more sustainable and efficient in terms of waste production and economy. In this study, we report a novel regiodivergent cyclization procedure to access two distinct azapolyaromatic regioisomers from 2-alkynylazobenzenes. The key to achieving this regiodivergence lies in the presence or absence of a gold catalyst. The irradiation with visible light of 2-alkynylazobenzenes in the presence of a Ir photocatalyst affords 11H-indolo[1,2-b]indazoles, whereas under similar conditions with AuCl3, indazolo[2,3-a]quinolines are produced. Control experiments and DFT calculations suggest that both transformations operate through different reaction mechanisms: the formation of 11H-indolo[1,2-b]indazoles involves a radical mechanism, whereas the formation of indazolo[2,3-a]quinolines appears to proceed predominantly through a polar mechanism. This transformation enables the one-step conversion of simple 2-alkynylazobenzenes into diverse azapolyaromatic structures via an intramolecular visible light-promoted process, holding significant potential for new nitrogenated heterocycles.
Org. Chem. Front. 2024
DOI: 10.1038/s41929-024-01204-6
