RESEARCH PAPER [Benzylamine-K 2 -C,N]1,2-Bis (Diphenylphosphino)-Propane-k 2 - P,P] Palladium}Perchlorate, Mononuclear Complex of Ortho-Palladated Derived from Benzylamine Ali Naghipour 1 • Seyyed Javad Sabounchei 2 • Mohsen Sayadi 1 • Mohammad Panahimehr 3 • Behrouz Notash 4 Received: 2 June 2015 / Accepted: 6 January 2016 / Published online: 16 May 2017 Ó Shiraz University 2017 Abstract This work reports the preparation of the mononuclear derivative [Pd(C 6 H 4 CH 2 NH 2 ) L](ClO 4 ) (L = dppp). The centrosymmetric mononuclear palladium complex obtained by the reaction of palladium(II) acetate with benzylamine in toluene produced the acetate cyclopalladated dimer of benzylamine. Metathesis reaction of this acetate-bridged cyclopalladated complex with NaCl in water and acetone gave N,C-orthopalladated [Pd(C 6 H 4- CH 2 NH 2 )(l-Cl)] 2 complex, which reacts with NaClO 4 / dppp to give the mononuclear derivative. The ortho-pal- ladation complex was characterized by various spectro- scopic techniques such as elemental analysis, IR, 1 H, 31 P, and 13 C NMR. The structures of N,C-metalated complex 3 were determined by X-ray diffraction study. Graphical Abstract Keywords Palladium(II) complexes Á C–H bond activation Á Ortho-palladation Á N,C-Chelating Á Benzylamine Á Crystal structure 1 Introduction One of the most important research areas in the field of organometallic chemistry is C-H bond activation in tran- sition metal complexes (Shilov and Shulpin 1997). Functionalization of the C–H group or forming the M–C bond (intermolecular or intramolecular), both including the methods C–H bond activation in transition metal complexes, is considered (Sabounchei et al. 2008, 2011; Karami et al. 2011, 2012; Weiss and Mohr 2011; Grice et al. 2011; Canty and Koten 1995; Garnovskii and Kharissov 2003; Nabavizadeh et al. 2011; Pugliese et al. 2006; Omae 2004). The ortho-palladation of aliphatic amines was initially reported by Cope and Friedrice (1968) to fail (a) when primary amines were used, (b) when electron-withdrawing substituents were present on the aromatic ring, or (c) when a six-membered ring was to be formed. These laws have been somewhat broken & Ali Naghipour naghipour2002@yahoo.com 1 Department of Chemistry, Faculty of Science, Ilam University, 69315-516 Ilam, Iran 2 Faculty of Chemistry, Bu-Ali Sina University, 65174 Hamedan, Iran 3 Young Researchers and Elite Club, Gachsaran Branch, Islamic Azad University, Gachsaran, Iran 4 Department of Chemistry, Shahid Beheshti University, G.C., Evin, 1983963113 Tehran, Iran 123 Iran J Sci Technol Trans Sci (2017) 41:129–133 DOI 10.1007/s40995-017-0210-4