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2. Nickel-Catalyzed Hydroborylative Polycyclization of Allenynes: an Atom-Economical and Diastereoselective Synthesis of Bicyclic 5-5 Fused Rings

Author

Manjón Mata, Inés, Quirós, M. Teresa, Velasco Juárez, Elena, Buñuel Magdalena, María Elena, Cárdenas, Diego J., and UAM. Departamento de Química Orgánica

Subjects
Ni, Hydroboration, Reaction mechanisms, General Chemistry, Química, Allenes, Cyclization
Abstract

A diastereoselective synthesis of borylated bicyclic 5-5 fused ring systems by a domino Ni-catalyzed hydroborylative polycyclization of allenynes has been developed. The reaction provides two new C−C and one C−B bonds and constitutes an atom-economical method. It occurs rapidly, in absence of inert atmosphere, with an inexpensive Ni-based catalyst and HBpin as boron source. The procedure showed excellent tolerance to functional groups and a wide scope. Derivatization of the borylated bicycles has been performed to explore the synthetic utility of the products. Experimental and DFT-calculation results suggest that the process starts by an oxidative cyclometallation involving Ni(0) and both the allene and the alkyne moieties, followed by a stereoselective σ-metathesis with HBpin. Formation of the second ring takes place through a non-fully coplanar 1,2-insertion into the Ni−H bond to give a nickelacyclohexene which finally evolves by reductive elimination. (Figure presented), We thank the support by MICIU (CTQ2016-79826-R and PID2019- 109088GB-I00) and for a FPI fellowship to I. M. M. We also thank the Centro de Computación Científica-UAM for technical assistance. We thank Juan Carlos Nieto-Carmona for helpful discussion and Prof. Fernando P. Cossío for helpful calculations

Published
2022

3. Pd-catalyzed C(sp3)-C(sp) bond formation in iodocyclobutenes

Author

Lázaro-Milla, C., Quirós, M. Teresa, Cárdenas, D. J., Almendros, Pedro, Lázaro-Milla, C., Quirós, M. Teresa, Cárdenas, D. J., and Almendros, Pedro

Abstract

A synthesis of skipped 1,4-enynes through functionalization of the cyclobutene core with alkynes has been achieved, suggesting an unusual pathway of oxidative addition in tertiary iodoalkane.

Published
2021

4. Triflyl-assisted reductive Pd-catalyzed Tsuji-Trost type reaction

Author

Ministerio de Ciencia, Innovación y Universidades (España), Ministerio de Economía y Competitividad (España), European Commission, Lázaro-Milla, Carlos, Quirós, M. Teresa, Cárdenas, D. J., Almendros, Pedro, Ministerio de Ciencia, Innovación y Universidades (España), Ministerio de Economía y Competitividad (España), European Commission, Lázaro-Milla, Carlos, Quirós, M. Teresa, Cárdenas, D. J., and Almendros, Pedro

Abstract

New (triflyl)cyclobutenes have been prepared by palladium-catalyzed hydrodetriflylation reaction using water and deuterium oxide as convenient hydrogen and deuterium sources. In addition, an investigation of the possible mechanism for this Tsuji-Trost type reaction of bis(triflyl)cyclobutenes has been facilitated by labelling studies and density functional theory (DFT) calculations.

Published
2020

5. Twists and turns of platinum-allene complexes: NMR techniques for the study of the dynamic behavior in solution

Author

Quirós, M. Teresa, Muñoz, María Paz, Christensen, Jeppe, and Coles, Simon J.

Subjects
Quantitative Biology::Biomolecules, 010405 organic chemistry, Chemistry, Stereochemistry, Ligand, Allene, Organic Chemistry, chemistry.chemical_element, 010402 general chemistry, 01 natural sciences, 0104 chemical sciences, Inorganic Chemistry, chemistry.chemical_compound, Computational chemistry, Intramolecular force, Reactivity (chemistry), Physics::Chemical Physics, Physical and Theoretical Chemistry, Platinum
Abstract

Classic (dynamic exchange lineshape analysis) and novel (SSTD NMR) NMR techniques have been applied in order to obtain the kinetic and thermo-dynamic parameters of the three main processes occurring in the fluxional behaviour of Pt-allene complexes with N-containing ligands, in four and five coordination mode, in solution. Our results show intramolecular helical and rotational movements, closely related to each other confirming η1 -staggered structures as possible intermediates. The ligand exchange in these complexes seems to occur via a ligand-independent dissociative mechanism, where coordinating solvents might be involved in the stabilisation of the intermediates. The differences observed in the interaction of allenes with other metals could be the basis to explain the divergent reactivity observed in platinum catalysed processes.

Published
2017

8. Gold/acid-co-catalyzed direct microwave-assisted synthesis of fused azaheterocycles from propargylic hydroperoxides

Author

Alcaide, Benito, Almendros, Pedro, Quirós, M. Teresa, Alcaide, Benito, Almendros, Pedro, and Quirós, M. Teresa

Abstract

The gold-acid-co-catalyzed synthesis of nine series of fused azaheterocycles with structural diversity starting from the same synthons as readily available propargylic hydroperoxides and aromatic amines has been achieved. The overall tandem process consists in a gold-catalyzed hydroperoxide rearrangement/Michael reaction followed by a final acid-catalyzed cyclization.

Published
2014

10. Unveiling the reactivity of propargylic hydroperoxides under gold catalysis

Author

Alcaide, Benito, Almendros, Pedro, Quirós, M. Teresa, López, Ramón, Menéndez, María I., Sochacka-Cwikla, Alesandra, Alcaide, Benito, Almendros, Pedro, Quirós, M. Teresa, López, Ramón, Menéndez, María I., and Sochacka-Cwikla, Alesandra

Abstract

Controlled gold-catalyzed reactions of primary and secondary propargylic hydroperoxides with a variety of nucleophiles including alcohols, phenols, 2-hydroxynaphthalene-1,4-dione, and indoles allow the direct and efficient synthesis of β-functionalized ketones. Moreover, the utility of some of the resulting products for the selective preparation of fused polycycles has been demonstrated. In addition, density functional theory (DFT) calculations and 18O-labeling experiments were performed to obtain an insight into various aspects of the controlled reactivity of propargylic hydroperoxides with external nucleophiles under gold catalysis. © 2012 American Chemical Society.

Published
2013

11. Gold-catalyzed oxycyclization of allenic carbamates: Expeditious synthesis of 1,3-oxazin-2-ones

Author

Alcaide, Benito, Almendros, Pedro, Quirós, M. Teresa, Fernández, Israel, Alcaide, Benito, Almendros, Pedro, Quirós, M. Teresa, and Fernández, Israel

Abstract

A combined experimental and computational study on regioselective gold-catalyzed synthetic routes to 1,3-oxazinan-2-ones (kinetically controlled products) and 1,3-oxazin-2-one derivatives (thermodynamically favored) from easily accessible allenic carbamates has been carried out. © 2013 Alcaide et al.

Published
2013

12. Gold- or palladium-catalyzed allene carbocyclization/functionalization: Simple and efficient synthesis of carbazoles

Author

Alcaide, Benito, Almendros, Pedro, Alonso, J. M., Quirós, M. Teresa, Gadzinski, P., Alcaide, Benito, Almendros, Pedro, Alonso, J. M., Quirós, M. Teresa, and Gadzinski, P.

Abstract

Gold- and palladium-catalyzed cyclization of easily accessible indole-tethered allenols allows the efficient synthesis of carbazole derivatives under mild conditions. Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Published
2011

14. Thermic Cope reaction of 2-azetidinone-tethered 1,5-dienes: synthesis of tetrahydroazocinones

Author

Almendros, Pedro, primary, Aragoncillo, Cristina, additional, Cabrero, Gema, additional, Callejo, Ricardo, additional, Carrascosa, Rocío, additional, Luna, Amparo, additional, Campo, Teresa Martínez del, additional, Pardo, M. Carmen, additional, Quirós, M. Teresa, additional, Redondo, M. Carmen, additional, Rodríguez-Ranera, Carolina, additional, Rodríguez-Vicente, Alberto, additional, and Ruiz, M. Pilar, additional

Published
2009
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15. Thermal Cope reaction of 2-azetidinone-tethered 1,5-dienes: synthesis of tetrahydroazocinones.

Author

Almendros, Pedro, Aragoncillo, Cristina, Cabrero, Gema, Callejo, Ricardo, Carrascosa, Rocío, Luna, Amparo, del Campo, Teresa Martínez, Pardo, M. Carmen, Quirós, M. Teresa, Redondo, M. Carmen, Rodríguez-Ranera, Carolina, Rodríguez-Vicente, Alberto, and Ruiz, M. Pilar

Subjects
*REARRANGEMENTS (Chemistry), *CHEMICAL bonds, *LACTAMS, *ORGANIC synthesis, *HETEROCYCLIC compounds, *CHEMICAL reactions, *PHYSICAL & theoretical chemistry
Abstract

We report herein full details of the first example of a Cope rearrangement in which the C3-C4 bond of the β-lactam nucleus is the central bond of the 1,5-hexadiene system, thus providing an easy and efficient entry to novel, and in some cases optically pure functionalized azocinones. [ABSTRACT FROM AUTHOR]

Published
2010

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