- -

Isolation and X-ray characterization of palladium N complexes in the guanylation ofaromatic amines. Mechanistic implications

RiuNet: Repositorio Institucional de la Universidad Politécnica de Valencia

Compartir/Enviar a

Citas

Estadísticas

  • Estadisticas de Uso

Isolation and X-ray characterization of palladium N complexes in the guanylation ofaromatic amines. Mechanistic implications

Mostrar el registro completo del ítem

Grirrane, A.; García Gómez, H.; Álvarez, E. (2013). Isolation and X-ray characterization of palladium N complexes in the guanylation ofaromatic amines. Mechanistic implications. Beilstein Journal of Organic Chemistry. 9:1455-1462. https://doi.org/10.3762/bjoc.9.165

Por favor, use este identificador para citar o enlazar este ítem: http://hdl.handle.net/10251/45654

Ficheros en el ítem

Thumbnail
Nombre: Grirrane;García;E ...
Tamaño: 2.334Mb
Formato: PDF
Descripción: Versión editorial
Abrir/Preview

Metadatos del ítem

Título: Isolation and X-ray characterization of palladium N complexes in the guanylation ofaromatic amines. Mechanistic implications
Autor: Grirrane, Abdessamad García Gómez, Hermenegildo Álvarez, Eleuterio
Entidad UPV: Universitat Politècnica de València. Departamento de Química - Departament de Química
Universitat Politècnica de València. Instituto Universitario Mixto de Tecnología Química - Institut Universitari Mixt de Tecnologia Química
Fecha difusión:
Resumen:
In the context of palladium-catalyzed guanylation of anilines herein, we have been able to characterize and isolate bis(anilino) and bis(guanidino)Pd(II) complexes using reaction conditions under which stoichiometric ...[+]
Palabras clave: Coordination chemistry , Guanylation reaction , Homogeneous catalysis , Palladium complexes , Reactive intermediates
Derechos de uso: Reconocimiento (by)
Fuente:
Beilstein Journal of Organic Chemistry. (issn: 1860-5397 )
DOI: 10.3762/bjoc.9.165
Editorial:
Beilstein-Institut
Versión del editor: http://dx.doi.org/10.3762/bjoc.9.165
Código del Proyecto:
info:eu-repo/grantAgreement/GVA//PROMETEO%2F2012%2F014/
info:eu-repo/grantAgreement/MINECO//CTQ2012-32315/ES/REDUCCION FOTOCATALITICA DEL DIOXIDO DE CARBONO/
Agradecimientos:
Financial support by the Spanish Ministry of Economy and competitiveness (Severo Ochoa and CTQ2012-36351) and Generalidad Valenciana (Prometeo 2012-014) is gratefully acknowledged.
Tipo: Artículo

References

Membrino, A., Paramasivam, M., Cogoi, S., Alzeer, J., Luedtke, N. W., & Xodo, L. E. (2010). Cellular uptake and binding of guanidine-modified phthalocyanines to KRAS/HRASG-quadruplexes. Chem. Commun., 46(4), 625-627. doi:10.1039/b918964e

Blondeau, P., Segura, M., Pérez-Fernández, R., & de Mendoza, J. (2007). Molecular recognition of oxoanions based on guanidinium receptors. Chem. Soc. Rev., 36(2), 198-210. doi:10.1039/b603089k

Thevissen, K., Pellens, K., De Brucker, K., François, I. E. J. A., Chow, K. K., Meert, E. M. K., … Cammue, B. P. A. (2011). Novel fungicidal benzylsulfanyl-phenylguanidines. Bioorganic & Medicinal Chemistry Letters, 21(12), 3686-3692. doi:10.1016/j.bmcl.2011.04.075 [+]
Membrino, A., Paramasivam, M., Cogoi, S., Alzeer, J., Luedtke, N. W., & Xodo, L. E. (2010). Cellular uptake and binding of guanidine-modified phthalocyanines to KRAS/HRASG-quadruplexes. Chem. Commun., 46(4), 625-627. doi:10.1039/b918964e

Blondeau, P., Segura, M., Pérez-Fernández, R., & de Mendoza, J. (2007). Molecular recognition of oxoanions based on guanidinium receptors. Chem. Soc. Rev., 36(2), 198-210. doi:10.1039/b603089k

Thevissen, K., Pellens, K., De Brucker, K., François, I. E. J. A., Chow, K. K., Meert, E. M. K., … Cammue, B. P. A. (2011). Novel fungicidal benzylsulfanyl-phenylguanidines. Bioorganic & Medicinal Chemistry Letters, 21(12), 3686-3692. doi:10.1016/j.bmcl.2011.04.075

Berlinck, R. G. S., Burtoloso, A. C. B., & Kossuga, M. H. (2008). The chemistry and biology of organic guanidine derivatives. Natural Product Reports, 25(5), 919. doi:10.1039/b507874c

Berlinck, R. G. S., & Kossuga, M. H. (2005). Natural guanidine derivatives. Natural Product Reports, 22(4), 516. doi:10.1039/b209227c

Bae, I., Han, H., & Chang, S. (2005). Highly Efficient One-Pot Synthesis ofN-Sulfonylamidines by Cu-Catalyzed Three-Component Coupling of Sulfonyl Azide, Alkyne, and Amine. Journal of the American Chemical Society, 127(7), 2038-2039. doi:10.1021/ja0432968

Omae, I. (2003). General Aspects of Tin-Free Antifouling Paints. Chemical Reviews, 103(9), 3431-3448. doi:10.1021/cr030669z

Liu, C., Zhou, S., Wang, S., Zhang, L., & Yang, G. (2010). Rare earth metal bis(trimethylsilyl)amido complexes bearing pyrrolyl-methylamide ligand. Synthesis, structure, and catalytic activity towards guanylation of amines. Dalton Transactions, 39(38), 8994. doi:10.1039/c0dt00246a

Ong, T.-G., Yap, G. P. A., & Richeson, D. S. (2003). Catalytic Construction and Reconstruction of Guanidines:  Ti-Mediated Guanylation of Amines and Transamination of Guanidines. Journal of the American Chemical Society, 125(27), 8100-8101. doi:10.1021/ja035716j

Montilla, F., Pastor, A., & Galindo, A. (2004). Guanylation of aromatic amines catalyzed by vanadium imido complexes. Journal of Organometallic Chemistry, 689(6), 993-996. doi:10.1016/j.jorganchem.2004.01.005

Zhang, W.-X., Li, D., Wang, Z., & Xi, Z. (2009). Alkyl Aluminum-Catalyzed Addition of Amines to Carbodiimides: A Highly Efficient Route to Substituted Guanidines. Organometallics, 28(3), 882-887. doi:10.1021/om801035t

Rowley, C. N., Ong, T.-G., Priem, J., Richeson, D. S., & Woo, T. K. (2008). Analysis of the Critical Step in Catalytic Carbodiimide Transformation: Proton Transfer from Amines, Phosphines, and Alkynes to Guanidinates, Phosphaguanidinates, and Propiolamidinates with Li and Al Catalysts. Inorganic Chemistry, 47(24), 12024-12031. doi:10.1021/ic801739a

Ong, T.-G., O’Brien, J. S., Korobkov, I., & Richeson, D. S. (2006). Facile and Atom-Efficient Amidolithium-Catalyzed C−C and C−N Formation for the Construction of Substituted Guanidines and Propiolamidines. Organometallics, 25(20), 4728-4730. doi:10.1021/om060539r

ZHU, X., XU, F., & SHEN, Q. (2009). An Efficient Guanylation of Aromatic Amines Catalyzed by Samarium Diiodide. Chinese Journal of Chemistry, 27(1), 19-22. doi:10.1002/cjoc.200990017

Wu, Y., Wang, S., Zhang, L., Yang, G., Zhu, X., Liu, C., … Rong, J. (2009). Efficient guanylation of aromatic and heterocyclic amines catalyzed by cyclopentadienyl-free rare earth metal amides. Inorganica Chimica Acta, 362(8), 2814-2819. doi:10.1016/j.ica.2008.12.030

Li, D., Guang, J., Zhang, W.-X., Wang, Y., & Xi, Z. (2010). Zn(OTf)2-catalyzed addition of amines to carbodiimides: efficient synthesis of guanidines and unpredicted formation of Zn–N amido species. Organic & Biomolecular Chemistry, 8(8), 1816. doi:10.1039/b923249b

Grirrane, A., Garcia, H., Corma, A., & Álvarez, E. (2012). Orthogonal CN Plus CC Tandem Reaction of Iodoanilines Leading to Styrylguanidines Catalyzed by Supported Palladium Nanoparticles. Chemistry - A European Journal, 18(47), 14934-14938. doi:10.1002/chem.201202823

Bon, V., Orysyk, S., & Pekhnyo, V. (2009). trans-Dichloridobis(4-methoxyaniline-κN)palladium(II). Acta Crystallographica Section E Structure Reports Online, 65(6), m673-m673. doi:10.1107/s1600536809018509

Anderson, R. A., & Einstein, F. W. B. (1978). Dichlorobis(di-tert-butylcarbodiimide)palladium(II). Acta Crystallographica Section B, 34(1), 271-272. doi:10.1107/s0567740878002770

Bodanszky, M. (1993). Peptide Chemistry. doi:10.1007/978-3-642-78206-0

[-]

recommendations

 

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

Mostrar el registro completo del ítem