- -

Few layer 2D pnictogens catalyze the alkylation of soft nucleophiles with esters

RiuNet: Repositorio Institucional de la Universidad Politécnica de Valencia

Compartir/Enviar a

Citas

Estadísticas

  • Estadisticas de Uso

Few layer 2D pnictogens catalyze the alkylation of soft nucleophiles with esters

Mostrar el registro sencillo del ítem

Ficheros en el ítem

Thumbnail
Nombre: LloretRivero-Cres ...
Tamaño: 1.973Mb
Formato: PDF
Descripción: Versión editorial
Abrir
dc.contributor.author Lloret, Vicent es_ES
dc.contributor.author Rivero-Crespo, Miguel Ángel es_ES
dc.contributor.author Vidal Moya, José Alejandro es_ES
dc.contributor.author Wild, Stefan es_ES
dc.contributor.author Domenech Carbo, Antonio es_ES
dc.contributor.author Heller, Bettina S. J. es_ES
dc.contributor.author Shin, Sunghwan es_ES
dc.contributor.author Steinrueck, Hans-Peter es_ES
dc.contributor.author Maier, Florian es_ES
dc.contributor.author Hauke, Frank es_ES
dc.contributor.author Varela, Maria es_ES
dc.contributor.author Hirsch, Andreas es_ES
dc.contributor.author Leyva Perez, Antonio es_ES
dc.contributor.author Abellán Sáez, Gonzalo es_ES
dc.date.accessioned 2022-05-27T18:05:20Z
dc.date.available 2022-05-27T18:05:20Z
dc.date.issued 2019-01-31 es_ES
dc.identifier.issn 2041-1723 es_ES
dc.identifier.uri http://hdl.handle.net/10251/182966
dc.description.abstract [EN] Group 15 elements in zero oxidation state (P, As, Sb and Bi), also called pnictogens, are rarely used in catalysis due to the difficulties associated in preparing well-structured and stable materials. Here, we report on the synthesis of highly exfoliated, few layer 2D phosphorene and antimonene in zero oxidation state, suspended in an ionic liquid, with the native atoms ready to interact with external reagents while avoiding aerobic or aqueous decomposition pathways, and on their use as efficient catalysts for the alkylation of nucleophiles with esters. The few layer pnictogen material circumvents the extremely harsh reaction conditions associated to previous superacid-catalyzed alkylations, by enabling an alternative mechanism on surface, protected from the water and air by the ionic liquid. These 2D catalysts allow the alkylation of a variety of acid-sensitive organic molecules and giving synthetic relevancy to the use of simple esters as alkylating agents. es_ES
dc.description.sponsorship We thank the European Research Council (ERC Starting Grant 804110 to G.A., and ERC Advanced Grant 742145 B-PhosphoChem to A.H.) for financial support. The research leading to these results was partially funded by the European Union Seventh Framework Program under grant agreement No. 604391 Graphene Flagship. G.A. has received financial support through the Postdoctoral Junior Leader Fellowship Program from "la Caixa" Banking Foundation (LCF/BQ/PI18/11630018). G.A. thanks support by the Deutsche Forschungsgemeinschaft (DFG; FLAG-ERA AB694/2-1), the Generalitat Valenciana (SEJI/2018/034 grant) and the FAU (Emerging Talents Initiative grant #WS16-17_Nat_04). Financial support by MINECO through the Excellence Unit Maria de Maeztu (MDM-2015-0538), Severo Ochoa (SEV-2016-0683) and RETOS (CTQ2014-55178-R) program is acknowledged. M.A.R.-C. thanks MINECO for the concession of a FPU fellowship. We also thank the DFG (DFG-SFB 953 "Synthetic Carbon Allotropes", Project A1), the Interdisciplinary Center for Molecular Materials (ICMM), and the Graduate School Molecular Science (GSMS) for financial support. Research at UCM sponsored by Spanish MINECO/FEDER grant MAT2015-066888-C3-3-R and ERC-PoC-2016 grant POLAR-EM. H.-P.S. thanks the European Research Council (ERC) under the European Union's Horizon 2020 research and innovation program for financial support, in the context of an Advanced Investigator Grant granted to him (Grant Agreement No. 693398-ILID). B.S.J.H. and S.S. acknowledge financial support by the DFG within the Cluster of Excellence "Engineering of Advanced Materials" (project EXC 315, Bridge Funding). F.M. acknowledges R. Ransom for very helpful discussions es_ES
dc.language Inglés es_ES
dc.publisher Nature Publishing Group es_ES
dc.relation.ispartof Nature Communications es_ES
dc.rights Reconocimiento (by) es_ES
dc.subject.classification QUIMICA ANALITICA es_ES
dc.title Few layer 2D pnictogens catalyze the alkylation of soft nucleophiles with esters es_ES
dc.type Artículo es_ES
dc.identifier.doi 10.1038/s41467-018-08063-3 es_ES
dc.relation.projectID info:eu-repo/grantAgreement/EC/FP7/604391/EU es_ES
dc.relation.projectID info:eu-repo/grantAgreement/Fundació Bancària Caixa d'Estalvis i Pensions de Barcelona//11630018/ es_ES
dc.relation.projectID info:eu-repo/grantAgreement/EC/H2020/693398/EU es_ES
dc.relation.projectID info:eu-repo/grantAgreement/GVA//SEJI%2F2018%2F034/ es_ES
dc.relation.projectID info:eu-repo/grantAgreement/EC/H2020/742145/EU es_ES
dc.relation.projectID info:eu-repo/grantAgreement/MINECO//MAT2015-066888-C3-3-R/ es_ES
dc.relation.projectID info:eu-repo/grantAgreement/EC/H2020/804110/EU es_ES
dc.relation.projectID info:eu-repo/grantAgreement/DFG//EXC 315/ es_ES
dc.relation.projectID info:eu-repo/grantAgreement/MINECO//MDM-2015-0538/ES/INSTITUTO DE CIENCIA MOLECULAR/ es_ES
dc.relation.projectID info:eu-repo/grantAgreement/FAU//WS16-17_Nat_04/ es_ES
dc.relation.projectID info:eu-repo/grantAgreement/DFG//FLAG-ERA AB694%2F2-1/ es_ES
dc.relation.projectID info:eu-repo/grantAgreement/MINECO//SEV-2016-0683//Programa Estatal de Fomento de la Investigación Científica y Técnica de Excelencia/ es_ES
dc.rights.accessRights Abierto es_ES
dc.contributor.affiliation Universitat Politècnica de València. Instituto Universitario Mixto de Tecnología Química - Institut Universitari Mixt de Tecnologia Química es_ES
dc.description.bibliographicCitation Lloret, V.; Rivero-Crespo, MÁ.; Vidal Moya, JA.; Wild, S.; Domenech Carbo, A.; Heller, BSJ.; Shin, S.... (2019). Few layer 2D pnictogens catalyze the alkylation of soft nucleophiles with esters. Nature Communications. 10:1-11. https://doi.org/10.1038/s41467-018-08063-3 es_ES
dc.description.accrualMethod S es_ES
dc.relation.publisherversion https://doi.org/10.1038/s41467-018-08063-3 es_ES
dc.description.upvformatpinicio 1 es_ES
dc.description.upvformatpfin 11 es_ES
dc.type.version info:eu-repo/semantics/publishedVersion es_ES
dc.description.volume 10 es_ES
dc.identifier.pmid 30705264 es_ES
dc.identifier.pmcid PMC6355817 es_ES
dc.relation.pasarela S\383594 es_ES
dc.contributor.funder European Commission es_ES
dc.contributor.funder Generalitat Valenciana es_ES
dc.contributor.funder Deutsche Forschungsgemeinschaft es_ES
dc.contributor.funder Ministerio de Economía y Competitividad es_ES
dc.contributor.funder Friedrich-Alexander-Universität Erlangen-Nürnberg es_ES
dc.contributor.funder Fundació Bancària Caixa d'Estalvis i Pensions de Barcelona es_ES
dc.description.references Mannix, A. J., Kiraly, B., Hersam, M. C. & Guisinger, N. P. Synthesis and chemistry of elemental 2D materials. Nat. Rev. Chem. 1, s41570–016 (2017). 0014–0016. es_ES
dc.description.references Ling, X., Wang, H., Huang, S., Xia, F. & Dresselhaus, M. S. The renaissance of black phosphorus. Proc. Natl Acad. Sci. 112, 4523–4530 (2015). es_ES
dc.description.references Pumera, M. & Sofer, Z. 2D monoelemental arsenene, antimonene, and bismuthene: beyond black phosphorus. Adv. Mater. 29, 1605299 (2017). es_ES
dc.description.references Ares, P., Palacios, J. J., Abellán, G., Gómez-Herrero, J. & Zamora, F. Recent progress on antimonene: a new bidimensional material. Adv. Mater. 30, 1703771 (2018). es_ES
dc.description.references Chen, P., Li, N., Chen, X., Ong, W.-J. & Zhao, X. The rising star of 2D black phosphorus beyond graphene: synthesis, properties and electronic applications. 2D Mater. 5, 014002 (2018). es_ES
dc.description.references Abellán, G. et al. Noncovalent functionalization of black phosphorus. Angew. Chem. Int. Ed. 55, 14557–14562 (2016). es_ES
dc.description.references Abellán, G. et al. Noncovalent functionalization and charge transfer in antimonene. Angew. Chem. Int. Ed. 56, 14389–14394 (2017). es_ES
dc.description.references Navalon, S., Dhakshinamoorthy, A., Alvaro, M. & Garcia, H. Carbocatalysis by graphene-based materials. Chem. Rev. 114, 6179–6212 (2014). es_ES
dc.description.references Navalon, S., Dhakshinamoorthy, A., Alvaro, M., Antonietti, M. & García, H. Active sites on graphene-based materials as metal-free catalysts. Chem. Soc. Rev. 46, 4501–4529 (2017). es_ES
dc.description.references Kiser, P. D. et al. Catalytic mechanism of a retinoid isomerase essential for vertebrate vision. Nat. Chem. Biol. 11, nchembio.1799 (2015). es_ES
dc.description.references Sanchez, C. et al. Lifetime and reactivity of an ultimate tamoxifen carcinogen: the tamoxifen carbocation. J. Am. Chem. Soc. 120, 13513–13514 (1998). es_ES
dc.description.references Watson, A. J. A. & Williams, J. M. J. The give and take of alcohol activation. Science 329, 635–636 (2010). es_ES
dc.description.references Trost, B. M. & Van Vranken, D. L. Asymmetric transition metal-catalyzed allylic alkylations. Chem. Rev. 96, 395–422 (1996). es_ES
dc.description.references Xu, X.-L. & Li, Z. Catalytic electrophilic alkylation of p‐quinones through a redox chain reaction. Angew. Chem. 129, 8308–8312 (2017). es_ES
dc.description.references Asao, N., Aikawa, H., Tago, S. & Umetsu, K. Gold-catalyzed etherification and friedel−crafts alkylation using ortho-alkynylbenzoic acid alkyl ester as an efficient alkylating agent. Org. Lett. 9, 4299–4302 (2007). es_ES
dc.description.references Manbeck, K. A., Kundu, S., Walsh, A. P., Brennessel, W. W. & Jones, W. D. Carbon–oxygen bond activation in esters by platinum(0): cleavage of the less reactive bond. Organometallics 31, 5018–5024 (2012). es_ES
dc.description.references Liu, X., Jia, J. & Rueping, M. Nickel-catalyzed C–O bond-cleaving alkylation of esters: direct replacement of the ester moiety by functionalized alkyl chains. ACS Catal. 7, 4491–4496 (2017). es_ES
dc.description.references Oliver-Meseguer, J., Cabrero-Antonino, J. R., Domínguez, I., Leyva-Pérez, A. & Corma, A. Small gold clusters formed in solution give reaction turnover numbers of 107 at room temperature. Science 338, 1452–1455 (2012). es_ES
dc.description.references Leyva-Pérez, A., Doménech-Carbó, A. & Corma, A. Unique distal size selectivity with a digold catalyst during alkyne homocoupling. Nat. Commun. 6, 6703 (2015). es_ES
dc.description.references Fortea-Pérez, F. R. et al. The MOF-driven synthesis of supported palladium clusters with catalytic activity for carbene-mediated chemistry. Nat. Mater. 16, 760–766 (2017). es_ES
dc.description.references Hanlon, D. et al. Liquid exfoliation of solvent-stabilized few-layer black phosphorus for applications beyond electronics. Nat. Commun. 6, 8563 (2015). es_ES
dc.description.references Gibaja, C. et al. Few-layer antimonene by liquid-phase exfoliation. Angew. Chem. Int. Ed. 55, 14345–14349 (2016). es_ES
dc.description.references Abellán, G. et al. Fundamental insights into the degradation and stabilization of thin layer black phosphorus. J. Am. Chem. Soc. 139, 10432–10440 (2017). es_ES
dc.description.references Kashin, A. S., Galkin, K. I., Khokhlova, E. A. & Ananikov, V. P. Direct observation of self-organized water-containing structures in the liquid phase and their influence on 5-(hydroxymethyl)furfural formation in ionic liquids. Angew. Chem. Int. Ed. 55, 2161–2166 (2016). es_ES
dc.description.references Favron, A. et al. Photooxidation and quantum confinement effects in exfoliated black phosphorus. Nat. Mater. 14, 826–832 (2015). es_ES
dc.description.references Gottfried, J. M. et al. Surface studies on the ionic liquid 1-ethyl-3-methylimidazolium ethylsulfate using X-ray photoelectron spectroscopy (XPS). Z. Für Phys. Chem. 220, 1439–1453 (2006). es_ES
dc.description.references Kuntz, K. L. et al. Control of surface and edge oxidation on phosphorene. ACS Appl. Mater. Interfaces 9, 9126–9135 (2017). es_ES
dc.description.references Ares, P. et al. Mechanical Isolation of highly stable antimonene under ambient conditions. Adv. Mater. 28, 6332–6336 (2016). es_ES
dc.description.references Fortin-Deschênes, M. et al. Synthesis of antimonene on germanium. Nano. Lett. 17, 4970–4975 (2017). es_ES
dc.description.references Walia, S. et al. Ambient protection of few‐layer black phosphorus via sequestration of reactive oxygen species. Adv. Mater. 29, 1700152 (2017). es_ES
dc.description.references Bodenes, L., Darwiche, A., Monconduit, L. & Martinez, H. The solid electrolyte interphase a key parameter of the high performance of Sb in sodium-ion batteries: comparative X-ray photoelectron spectroscopy study of Sb/Na-ion and Sb/Li-ion batteries. J. Power Sources 273, 14–24 (2015). es_ES
dc.description.references Powell, C. J. Recommended Auger parameters for 42 elemental solids. J. Electron Spectrosc. Relat. Phenom. 185, 1–3 (2012). es_ES
dc.description.references Yates, K. Kinetics of ester hydrolysis in concentrated acid. Acc. Chem. Res. 4, 136–144 (1971). es_ES
dc.description.references Chen, X. et al. Synthesis of tert-butyl acetate via eco-friendly additive reaction over mesoprous silica catalysts with balanced Brönsted and Lewis acid sites. J. Porous Mater. 23, 255–262 (2016). es_ES
dc.description.references King, D. L., Cooper, M. D. & Faber, M. A. Acid catalyzed process. US Patent 4, 868–343 (1989). es_ES
dc.description.references Bandini, M., Fagioli, M. & Umani-Ronchi, A. Solid acid-catalysed michael-type conjugate addition of indoles to electron-poor CC bonds: towards high atom economical semicontinuous processes. Adv. Synth. Catal. 346, 545–548 (2004). es_ES
dc.description.references Bartoli, G. et al. Unusual and unexpected reactivity of t-butyl dicarbonate (Boc2O) with alcohols in the presence of magnesium perchlorate. a new and general route to t-butyl ethers. Org. Lett. 7, 427–430 (2005). es_ES
dc.description.references Huang, Y. et al. Interaction of black phosphorus with oxygen and water. Chem. Mater. 28, 8330–8339 (2016). es_ES
dc.description.references Wang, Y. et al. Degradation of black phosphorus: a real-time 31 P NMR study. 2D Mater. 3, 035025 (2016). es_ES
dc.description.references Wang, L., Sofer, Z. & Pumera, M. Voltammetry of layered black phosphorus: electrochemistry of multilayer phosphorene. ChemElectroChem 2, 324–327 (2015). es_ES
dc.description.references Olah, G. A. & Kiovsky, T. E. Stable carbonium ions. LI. Fluorobenzenonium ions. J. Am. Chem. Soc. 89, 5692–5694 (1967). es_ES
dc.description.references Jerry, M. Advanced Organic Chemistry: Reactions Mechanisms and Structure. (McGraw Hill Book Company, New York, 1968). es_ES
dc.description.references Pavelich, W. A. & Taft, R. W. Jr. The evaluation of inductive and steric effects on reactivity. the methoxide ion catalyzed rates of methanolysis of /-menthyl esters in methanol. J. Am. Chem. Soc. 79, 4935–4940 (1957). es_ES
dc.description.references Üzengi Aktürk, O., Aktürk, E. & Ciraci, S. Effects of adatoms and physisorbed molecules on the physical properties of antimonene. Phys. Rev. B 93, 035450 (2016). es_ES
dc.description.references Wang, H. et al. Ultrathin black phosphorus nanosheets for efficient singlet oxygen generation. J. Am. Chem. Soc. 137, 11376–11382 (2015). es_ES
dc.description.references Mayorga-Martinez, C. C., Mohamad Latiff, N., Eng, A. Y. S., Sofer, Z. & Pumera, M. Black phosphorus nanoparticle labels for immunoassays via hydrogen evolution reaction mediation. Anal. Chem. 88, 10074–10079 (2016). es_ES
dc.description.references Hu, J. et al. Band gap engineering in a 2D material for solar-to-chemical energy conversion. Nano Lett. 16, 74–79 (2015). es_ES
dc.description.references Lei, W. et al. Bandgap- and local field-dependent photoactivity of Ag/black phosphorus nanohybrids. ACS Catal. 6, 8009–8020 (2016). es_ES
dc.description.references Caporali, M. et al. Decoration of exfoliated black phosphorus with nickel nanoparticles and its application in catalysis. Chem. Commun. 53, 10946–10949 (2017). es_ES
dc.description.references Niedermaier, I., Kolbeck, C., Steinrück, H.-P. & Maier, F. Dual analyzer system for surface analysis dedicated for angle-resolved photoelectron spectroscopy at liquid surfaces and interfaces. Rev. Sci. Instrum. 87, 045105 (2016). es_ES
dc.description.references Shard, A. G. Detection limits in XPS for more than 6000 binary systems using Al and Mg Kα X-rays. Surf. Interface Anal. 46, 175–185 (2014). es_ES


Este ítem aparece en la(s) siguiente(s) colección(ones)

Mostrar el registro sencillo del ítem