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Updated: Jan 20, 2026
Amide Coupling Reaction for the Synthesis of Bispyridine-based Ligands and Their Complexation to Platinum as Dinuclear Anticancer Agents
Published on: May 28, 2014
Synthesis of (Arylmido)niobium(V) Complexes Containing Ketimide, Phenoxide Ligands, and Some Reactions with Phenols
Natta Srisupap1, Kritdikul Wised1, Ken Tsutsumi1
1Department of Chemistry, Faculty of Science, Tokyo Metropolitan University, 1-1 Minami Osawa, Hachioji, Tokyo 192-0397, Japan.
Abstract:
Reactions of Nb(NAr)(N=C Bu2)3 (3a, Ar = 2,6-Me2C6H3) with 1.0, 2.0, or 3.0 equiv of Ar'OH (Ar' = 2,6- Pr2C6H3) afforded Nb(NAr)(N=C Bu2)2(OAr'), Nb(NAr)(N=C Bu2)(OAr')2, or Nb(NAr)(OAr')3, respectively (at 25 °C), whereas the reaction with 2.0 equiv of 2,6- Bu2C6H3OH afforded Nb(NAr)(N=C Bu2)2(O-2,6- Bu2C6H3) upon heating (70 °C) without the formation of bis(phenoxide) and the reaction of 3a with 2.0 equiv of 2,4,6-Me3C6H2OH afforded Nb(NAr)(N=C Bu2)(O-2,4,6-Me3C6H2)2(HN=C Bu2). Similar reactions of 3a with 1.0 equiv of (CF3)3COH or 2.0 equiv of (CF3)2CHOH afforded Nb(NAr)(N=C Bu2)2[OC(CF3)3](HN=C Bu2) or Nb(NAr)(N=C Bu2)[OCH(CF3)2]2(HN=C Bu2), respectively. On the basis of their structural analyses and the reaction chemistry, it was suggested that these reactions proceeded via coordination of phenol (alcohol) to Nb and the subsequent proton (hydrogen) transfer to the ketimide (N=C Bu2) ligand. The reaction of Nb(NAr)(N=C Bu2)2(OAr') with 1.0 equiv of 2,4,6-Me3C6H2OH gave the disproportionation products Nb(NAr)(N=C Bu2)(OAr')2 and Nb(NAr)(N=C Bu2)(O-2,4,6-Me3C6H2)2(HN=C Bu2) with 1:1 ratio, clearly indicating the presence of the above mechanism and the fast equilibrium (between the ketimide and the phenoxide). The reaction of 3a with 1.0 or 2.0 equiv of C6F5OH afforded Nb(N=C Bu2)2(OC6F5)3(HN=C Bu2) as the sole isolated product, which was formed from once generated Nb(NAr)(N=C Bu2)2(OC6F5)(HN=C Bu2) by treating with C6F5OH.
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