Nashrieh Shimi va Mohandesi Shimi Iran

Nashrieh Shimi va Mohandesi Shimi Iran

The Synthesis of Benzhydrol Derivatives via Phenylation of Aromatic Aldehydes in the Presence of DPPE-Copper Nanometal Complex

Document Type : Research Article

Authors
Akram Ashouri
Saadi Samadi
Somayeh Pourian
Pegah Rezaei
Department of Chemistry, Faculty of Science, University of Kurdistan, Sanandaj, I.R. IRAN
Abstract
Cu/Fe3O4 magnetic nanometal was synthesized and characterized by FT-IR spectroscopy, Energy Diffraction X-ray (EDX) spectroscopy, Electron Scanning Microscope (SEM), and Vibrating Sample Magnetometer (VSM). In continue, the complex of synthesized magnetic nanometal with the dppe(1, 2-diphenylphosphine ethane) ligand was used in 1, 2-nucleophilic addition of aryl group to aromatic aldehydes using phenylboronic acid. Alcoholic products were obtained with a good yield (up to 95%) in an acceptable time (up to 24 hours). The catalyst was magnetically recovered and reused in the addition reaction five times without a significant reduction in catalytic activity and yield. The structure of products was determined using melting point and 1H NMR, 13C NMR, and FT-IR spectroscopies
Keywords
Magnetic nanoparticles
Phenylation addition
Boronic acid
Benzhydrol derivatives
Organometallic reagent
Phosphine ligand
Subjects
[1] Dosa P.I., Ruble J.C., Fu G.C., Planar−Chiral Heterocycles as Ligands in Metal-Catalyzed Processes: Enantioselective Addition of Organozinc Reagents to Aldehydes, J. Org. Chem. 62:  444-445 (1997.(
[2] Sakai M., Hayashi H., Miyaura N., Rhodium-Catalyzed Conjugate Addition of Aryl-or 1-Alkenylboronic Acids to Enones, Organometallics, 16: 4229-4231 (1997).
[3] Yamamoto T., Ohta T., Ito Y., Palladium-Catalyzed Addition of Arylboronic Acids to Aldehydes, Org. Lett. 7: 4153-4155 (2005).  
[4] Lai C.W., et al., Iridium‐Complex‐Functionalized Fe3O4/SiO2 Core/Shell Nanoparticles:
A Facile Three‐in‐one System in Magnetic Resonance Imaging, luminescence Imaging, and Photodynamic Therapy, Small. 4: 218-224 (2008(.
[5] Long Y ,. et al.,  Pt NPs Immobilized on Core–Shell Magnetite Microparticles: Novel and Highly Efficient Catalysts for the Selective Aerobic Oxidation of Ethanol and Glycerol
in Water, Dalton Trans. 44: 8660-8668 (2015(.
[6] Dayan S., Arslan F., Ozpozan, N.K., Ru (II) Impregnated Al2O3, Fe3O4, SiO2 and N-Coordinate Ruthenium (II) Arene Complexes: Multifunctional Catalysts in the Hydrogenation of Nitroarenes and the Transfer Hydrogenation of Aryl Ketones, Appl. Catal., B. 164:  305-315 (2015).
[7] Han J., et al., Hydrothermal Synthesis of Cu-Fe3O4 Nanocomposites Towards Catalytic Degradation of Organic Dyes, J. Nanoparticle Res.19: 233 (2017(.
[8] Liu Y., Liu Z., Cui Y., An Efficient Nanoparticle‐Supported and Magnetically Recoverable Copper (I) Catalyst for Synthesis of Furans from Ene‐Yne‐Ketone, Chin. J. Chem. 33: 175-180 (2015.(
[9] Mirabedini M., Motamedi E., Kassaee M.Z., Magnetic CuO Nanoparticles Supported on Graphene Oxide as an Efficient Catalyst for A3-Coupling Synthesis of Propargylamines, Chin. Chem. Lett. 26: 1085-1090 (2015(.
[10] Yasukawa T., et al., Asymmetric Arylation of Imines Catalyzed by Heterogeneous Chiral Rhodium Nanoparticles, Org. Lett. 18: 2716-2718 (2016(.
[11] Zhao H., et al., Recyclable and Reusable Pd (OAc) 2/P (1-Nap) 3/[bmim][PF6]/H2O System for the Addition of Arylboronic Acids to Aldehydes, J. Organomet. Chem. 777: 50-56 (2015(.
[12] Wu J., et al., Cobalt (II) Coordination Polymer as a Precatalyst for Selective Hydroboration of Aldehydes, Ketones, and Imines,  J. Org. Chem. 83: 9442-9448 (2018(.
[13] Slocum D., et al., Halogen/Lithium Exchange in Hydrocarbon Media; Basic and Continuous Reactor Studies, Tetrahedron Letters. 51: 4793-4796 (2010.(
[14] Kelly D.P., Spear R.J., Carbon-13 NMR Studies of Carbocations. Determination of σ+ Ortho Constants from 13C Spectra of Benzhydryl Cations, Aust. J. Chem. 30: 1993-2004,(1977(.
[15] Zhang X., et al., Synthesis of a Fe3O4–CuO@meso-SiO2 Nanostructure as a Magnetically Recyclable and Efficient Catalyst for Styrene Epoxidation, J. Am. Chem. Soc. 4: 3082-3089 (2014(.
[16] Beckwith A.L., Zavitsas A. A., Allylic Oxidations by Peroxy Esters Catalyzed by Copper Salts. The Potential for Stereoselective Syntheses, J. Am. Chem. Soc. 108: 8230-8234 (1986(.
[17] García-Cabeza A.L., et al., Allylic Oxidation of Alkenes Catalyzed by a Copper–Aluminum Mixed Oxide, Org. Lett. 16: 1598-1601 (2014(.
[18] Hartwig J.F., Larsen M.A., Undirected, Homogeneous C–H Bond Functionalization: Challenges and Opportunities, ACS Cent. Sci. 2: 281-292 (2016(.
[19] Mayoral J.A., Rodríguez‐Rodríguez S., Salvatella L., Theoretical Insights into Enantioselective Catalysis: The Mechanism of the Kharasch–Sosnovsky Reaction, Chem. Eur. J. 14:  9274-9285 (2008(.
[20] Shi E., Tetrabutylammonium Iodide Catalyzed Synthesis of Allylic Ester with Tert-Butyl Hydroperoxide as an Oxidant, Org. Lett., 14: 3384-3387 (2012(.
[21] Qin C., Wu H., Cheng J., Chen X.A., Liu M., Zhang W., Ding J., The Palladium-Catalyzed Addition of Aryl-and Heteroarylboronic Acids to Aldehydes, J. Org. Chem., 72: 4102-4107 (2007).
[22] Gois P.M., Trindade A.F., Veiros L.F., Andre V., Duarte M.T., Afonso C.A., Cloke F.G.N., Tuning the Reactivity of Dirhodium (II) Complexes with Axial N‐Heterocyclic Carbene Ligands: The Arylation of Aldehydes, Angew. Chem., 46: 5750-5753, (2007).
[23] Tran B.L., Driess M., Hartwig J.F., Copper-Catalyzed Oxidative Dehydrogenative Carboxylation of Unactivated Alkanes to allylic Esters via Alkenes, J. Am. Chem. Soc., 136: 17292-17301 (2014(.
[24] Wang C.Y., et al., Copper-Catalyzed Oxidative Coupling of Acids with Alkanes Involving Dehydrogenation: Facile Access to Allylic Esters and Alkylalkenes, Chem. Comm., 51: 2361-2363 (2015.(