Jesús A. Molina de la Torre

Universidad de Valladolid

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Ana C. Albéniz

Universidad de Valladolid

Kathleen Grabow

Leibniz Institute for Catalysis

Shaolin Zhou

Central China Normal University

Kathrin Junge

Leibniz Institute for Catalysis

Yuehui Li

Shanghai Jiao Tong University

Matthias Beller

Leibniz Institute for Catalysis

Ursula Bentrup

Leibniz Institute for Catalysis

Angelika Brückner

Leibniz Institute for Catalysis

Ignacio Pérez‐Ortega

University of Manchester

ÁB

Álvaro Beltrán

Universidad de Sevilla

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Leibniz Institute for Catalysis

University of Rostock

Universidad de Valladolid

Universidad de Huelva

Comisión Sectorial de Investigación Científica

Robert Bosch (Germany)

Rostocker Zentrum zur Erforschung des Demografischen Wandels

Universidad de Sevilla

Institut Català d'Investigació Química

Universitat Autònoma de Barcelona

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p-Bromoaryl- and ω-bromoalkyl-VA-PNBs: suitable starting materials for the functionalization of vinylic addition polynorbornenes via palladium-catalyzed cross-coupling reactions

RSC Advances (2016)

Sheila Martínez‐Arranz Eduardo Sánchez-Pérez Jesús A. Molina de la Torre Ignacio Pérez‐Ortega Ana C. Albéniz

New routes to functionalize the robust VA-polynorbornene skeleton by Pd-catalyzed cross-coupling reactions usep-bromoaryl- and ω-bromoalkyl-VA-PNBs as versatile starting materials.

Surface Modification

Coupling reaction

10.1039/c6ra23123c

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Citations (14)

Selective Reduction of Amides to Amines by Boronic Acid Catalyzed Hydrosilylation

Angewandte Chemie (2013)

Yuehui Li Jesús A. Molina de la Torre Kathleen Grabow Ursula Bentrup Kathrin Junge

Vielseitig und metallfrei: Benzothiophen-Boronsäuren katalysieren die Reduktion tertiärer, sekundärer und primärer Amide durch ein Hydrosilan. In der Reaktion wird eine Vielzahl von funktionellen Gruppen toleriert. As a service to our authors and readers, this journal provides supporting information supplied by the authors. Such materials are peer reviewed and may be re-organized for online delivery, but are not copy-edited or typeset. Technical support issues arising from supporting information (other than missing files) should be addressed to the authors. Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.

Hydrosilylation

Boronic acid

10.1002/ange.201304495

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Citations (27)

Vinylic Addition Polynorbornene as Support for N‐Heterocyclic Carbene Palladium Complexes: Use as Reservoir of Active Homogeneous Catalytic Species in C−C Cross‐Coupling Reactions

ChemCatChem (2016)

Jesús A. Molina de la Torre Ana C. Albéniz

Abstract A vinylic addition polynorbornene (VA‐PNB) functionalized with imidazolium groups can be used to synthesize a well‐defined supported palladium carbene complex. This complex is a suitable precatalyst for Suzuki and Negishi cross‐coupling reactions, and it can be reused. A close look at how the catalysis works reveals that palladium aggregates form on the polymer surface after the first catalytic reaction. However, they are not easily washed out and serve as a source of small amounts of homogeneous palladium active species (about 0.01% mol), which are responsible for the catalysis. The recovered polymer can be reused several times although increased induction and reaction times are observed in consecutive uses from one run to the next. The reaction was followed up by in situ IR spectroscopy by using the ν (C−Br) absorption band of the electrophile, so there is no need for an additional functional group to apply this technique.

Negishi coupling

Coupling reaction

Homogeneous Catalysis

10.1002/cctc.201600194

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Citations (11)

Vinylic addition polynorbornene as catalyst support: applications in organocatalysis and palladium-catalyzed c-c coupling reactions

Jesús A. Molina de la Torre

1 Relevance of catalysis 1.2 Supported catalysis 1.3 Polymer-supported catalysts v 5.4.5 Synthesis of polymer-supported diimine-palladium complexes Synthesis of [{VA-CopNBNB(C=N-Ar) 2 }PdClMe] (39) Synthesis of [{VA-CopNBNB(C=N-Ar) 2 }Pd(CF 3 CO 2 ) 2 ] (40) 5.4.6 Polymerization reactions with 39 Polymerization of ethylene Copolymerization of ethylene with methyl acrylate 5.4.7 General procedure for the Suzuki reactions followed by in situ IR.Resumen Presentación Capítulo 1 Introducción general.Capítulo 2 Carbenos N-Heterocíclicos soportados en polinorbornenos de adición vinílica.Usos en organocatálisis.Capítulo 3 Complejos Pd-NHC soportados en polinorbornenos de adición vinílica.Usos en reacciones de acoplamiento C-C.Capítulo 4 Reducción de complejos paladio-arilo inducida por el disolvente.Capítulo 5 Complejos Pd-diimina soportados en polinorbornenos de adición vinílica.Conclusiones

10.35376/10324/21067

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α‐Diimine–Palladium Complexes Incorporated in Vinylic‐Addition Polynorbornenes: Synthesis and Catalytic Activity

European Journal of Inorganic Chemistry (2017)

Jesús A. Molina de la Torre Ana C. Albéniz

α‐Diimine polymeric ligands have been synthesized using the bicyclic norbornane structure, present in vinylic‐addition polynorbornene (VA‐PNB). The VA‐PNB–diimine ligands have been prepared by functionalization of the copolymer obtained by Ni‐catalyzed polymerization of norbornene and norbornenylcarbonate. Immobilized palladium complexes of the type VA‐PNB–diimine–PdX 2 have been prepared, and their catalytic activity has been tested. The trifluoroacetato complex (X = CF 3 COO) can be used as a recyclable precatalyst in the Suzuki reaction. It is the source of minute amounts of homogeneous palladium active species, which carry out the catalysis with high turnover numbers. The recovered polymeric complex can be reused several times with no significant loss of activity. The polymeric analogue to Brookhart's catalyst, VA‐PNB–diimine–PdMeCl, can also polymerize ethylene, although it is less active than its monomeric counterparts.

Diimine

Norbornene

Addition polymer

10.1002/ejic.201700323

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Citations (11)

Trispyrazolylborate Ligands Supported on Vinyl Addition Polynorbornenes and Their Copper Derivatives as Recyclable Catalysts

Chemistry - A European Journal (2018)

Jesús A. Molina de la Torre Ignacio Pérez‐Ortega Álvaro Beltrán Manuel R. Rodríguez M. Mar Díaz‐Requejo

Polynorbornenes prepared by vinyl addition polymerization and bearing pendant alkenyl groups serve as skeletons to support trispyrazolylborate ligands (Tpx ) built at those alkenyl sites. Reaction with CuI in acetonitrile led to VA-PNB-Tpx Cu(NCMe) (VA-PBN=vinyl addition polynorbornene) with a 0.8-1.4 mmol incorporation of Cu per gram of polymer. The presence of tetracoordinated copper(I) ions was been assessed by FTIR studies on the corresponding VA-PNB-Tpx Cu(CO) adducts, in agreement with those on discrete Tpx Cu(CO). The new materials were employed as heterogeneous catalysts in several carbene- and nitrene-transfer reactions, showing a behavior similar to that of the homogeneous counterparts but also being recycled several times maintaining a high degree of activity and selectivity. This is the first example of supported Tpx ligands onto polymeric supports with catalytic applications.

Nitrene

10.1002/chem.201803852

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Citations (9)

N‐Heterocyclic Carbenes Supported on Vinylic Addition Polynorbornene: A Recyclable and Recoverable Organocatalyst

ChemCatChem (2014)

Jesús A. Molina de la Torre Ana C. Albéniz

Abstract A bromoalkyl functionalized vinylic addition polynorbornene has been used as an inert new scaffold to support imidazolium salts by straightforward nucleophilic substitution using different imidazoles ImR (R=Me, mesityl, 2,6‐ i Pr 2 C 6 H 3 ). These polymers, VA‐PNB‐(CH 2 ) 4 ImRBr, are precursors of N‐heterocyclic carbenes which are useful as heterogeneous organocatalysts. The polymeric carbenes have been tested in two model reactions: The synthesis of saturated esters from α,β‐unsaturated aldehydes and the conjugate umpolung reaction of α,β‐unsaturated aldehydes for the synthesis of γ‐butyrolactones. The supported catalyst (R=mesityl) is fully recyclable and can be recovered as an imidazolium salt and stored for further use.

Umpolung

Conjugate

10.1002/cctc.201402767

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Citations (16)

Selective Reduction of Amides to Amines by Boronic Acid Catalyzed Hydrosilylation

Angewandte Chemie International Edition (2013)

Yuehui Li Jesús A. Molina de la Torre Kathleen Grabow Ursula Bentrup Kathrin Junge

Not a 'B'ore! Benzothiophene-based boronic acids catalyze the reduction of tertiary, secondary, and primary amides in the presence of a hydrosilane. The reaction demonstrates good functional-group tolerance.

Benzothiophene

Hydrosilylation

Boronic acid

Primary (astronomy)

Functional group

Selective Reduction

10.1002/anie.201304495

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Citations (115)

ChemInform Abstract: Selective Reduction of Amides to Amines by Boronic Acid Catalyzed Hydrosilylation.

ChemInform (2014)

Yuehui Li Jesús A. Molina de la Torre Kathleen Grabow Ursula Bentrup Kathrin Junge

Abstract A general method for the hydrogenative deoxygenation of tertiary, secondary, and primary amides into the corresponding amines is developed.

Deoxygenation

Hydrosilylation

Primary (astronomy)

Boronic acid

Tertiary alcohols

Selective Reduction

10.1002/chin.201413038

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Solvent-Induced Reduction of Palladium-Aryls, a Potential Interference in Pd Catalysis

Organometallics (2013)

Jesús A. Molina de la Torre Pablo Espinet Ana C. Albéniz

The decomposition of the Pd-aryl complex (NBu4)2[Pd2(μ-Br)2Br2(C6F5)2] (1) to the reduction product C6F5H was checked in different solvents and conditions. 1 is not stable in N-alkyl amides (DMF, NMP, DMA), cyclohexanone, and diethers (1,4-dioxane, DME) at high temperatures (above 80 °C). Other solvents such as nitriles, THF, water, or toluene are safe, and no significant decomposition occurs. The solvent is the source of hydrogen, and the decomposition mechanisms have been identified by analyzing the reaction products coming from the solvent. β-H elimination involving the methyl group in a N-coordinated amide is the predominant pathway for amides. An O-coordinated diether undergoes β-H elimination and subsequent deprotonation of the resulting oxonium salt to give an enol ether. A palladium enolate from cyclohexanone leads to cyclohexenone, a reaction favored by the presence of a base. Oxygen strongly increases the extent of decomposition, and we propose this occurs by reoxidation of the Pd(0) species formed in the process and regeneration of active Pd(II) complexes.

Silyl enol ether

Reductive elimination

Mesitylene

Transmetalation

Oxonium ion

Amide

10.1021/om400713y

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Citations (43)