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The six-coordinated bis- o -iminosemiquinone complex, NiL 2  BIS , in which L BIS is the o -iminosemiquinone 1-electron oxidized form of the tridentate o -aminophenol benzoxazole-based ligand H 2 L BAP , was synthesized and characterized. The crystal structure of the complex reveals octahedral geometry with a NiN 4 O 2 coordination sphere in which Ni(ii) has been surrounded by two tridentate L BIS ligands. This compound exhibits ( S  Ni = 1) with both spin and orbital contribution to the magnetic moment and antiferromagnetic coupling between two electrons on two L BIS ligands which results in a triplet spin ground state ( S = 1). The electronic transitions and the electrochemical behavior of this open-shell molecule are presented here, based on experimental observations and theoretical calculations. The electrochemical behavior of NiL 2  BIS was investigated by cyclic voltammetry and indicates ligand-centered redox processes. Three-component coupling of aldehydes, amines and alkynes (A 3 -coupling) was studied in the presence of the NiL 2  BIS complex, and the previously reported four-coordinated bis- o -iminosemiquinone NiL 2  NIS . Furthermore, among these two o -iminobenzosemiquinonato(1-) complexes of Ni(ii) (NiL 2  NIS and NiL 2  BIS ), NiL 2  NIS was found to be an efficient catalyst in A 3 -coupling at 85 °C under solvent-free conditions and can be recovered and reused for several cycles with a small decrease in activity.

rsc advances

Biradical <i>o</i>-iminobenzosemiquinonato(1−) complexes of nickel(<scp>ii</scp>): catalytic activity in three-component coupling of aldehydes, amines and alkynes

Biradical o-iminobenzosemiquinonato(1−) complexes of nickel(ii): catalytic activity in three-component coupling of aldehydes, amines and alkynes