One-step templated synthesis of chiral organometallic salicyloxazoline complexes

BMC Chem. 2019 Apr 4;13(1):51. doi: 10.1186/s13065-019-0565-z. eCollection 2019 Dec.

Abstract

Background: The general approach to the synthesis of metal complexes begins with ligand synthesis, followed by ligand reaction with metal salts to afford organometallic complexes. Our research group first reported a one-pot multicomponent synthesis of chiral oxazolinyl-zinc complexes, in the presence of a large amount of ZnCl2 (0.4-2.6 equiv.), with the yields of some products reaching 90%.

Results: Our prior strategy was extended to use copper, cobalt, nickel, manganese, palladium or platinum salts as the third component. The one-step method used 1.0 equivalent of a metal salt, such as M(OAc)2·nH2O or MCl2·nH2O (M: Cu, Co, Ni, Pd or Pt, n = 1, 2 or 4), as a reagent to generate chiral salicyloxazoline complexes 1-8 in the reaction of 2-cyanophenol with different d- and l-amino alcohols.

Conclusion: Complexes 1-8 were obtained using a one-pot method with a sequential strategy. The reaction outcome was demonstrated for three-component reactions between metal salts, amino alcohols and 2-hydroxybenzonitrile to afford organometallic complexes in good yields (65-95%).

Keywords: 2-Cyanophenol; Metal salts; One-step method; Salicyloxazoline complexes; d- and l-Amino alcohols.