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Six-membered pincer nickelacycle complexes have been synthesized and employed for the catalytic C–H bond alkylation of benzothiazole. The pincer nickelacycle, \(\{\kappa ^{\mathrm{P}},\kappa ^{\mathrm{C}}, \kappa ^{\mathrm{P}}\hbox {-}(2\hbox {-}{}^{i}\hbox {Pr}_{2}\hbox {POCH}_{2}\hbox {-C}_{6}\hbox {H}_{3}\hbox {-}6\hbox {-CH}_{2}\hbox {OP}^{i}\hbox {Pr}_{2})\}\hbox {NiBr}\), \([({}^{i}\hbox {Pr}_{4}\hbox {-POCCCOP})\hbox {NiBr}\quad (\mathbf{2})]\) was synthesized by the reaction of 1,\(3\hbox {-}^{i}\hbox {Pr}_{2}\hbox {POCH}_{2}\hbox {-C}_{6}\hbox {H}_{4}\hbox {-CH}_{2}\hbox {OP}^{i}\hbox {Pr}_{2}\) \([({}^{i}\hbox {Pr}_{4}\hbox {-POCCCOP})-\hbox {H}\,\,(\mathbf{1})]\) with \((\hbox {CH}_{3}\hbox {CN})_{2}\hbox {NiBr}_{2}\) in the presence of \(\hbox {Et}_{3}\hbox {N}\) via the C(2)–H activation on ligand 1. Treatment of \([({}^{i}\hbox {Pr}_{4}\hbox {-POCCCOP})\hbox {NiBr}]\,\,(\mathbf{2})\) with AgOAc afforded the complex \([({}^{i}\hbox {Pr}_{4}\hbox {-POCCCOP})\hbox {Ni}(\hbox {OAc})]\) (3) in good yield. Both the complexes 2 and 3 were characterized by \({}^{1}\hbox {H}\), \({}^{13}\hbox {C}\) and \({}^{31}\hbox {P}\)-NMR spectral analysis. Further, the molecular structures of complexes 2 and 3 were established by X-ray crystallography. The complex 2 was found to be an active catalyst for the C–H bond alkylation of benzothiazole with alkyl halides containing \(\beta \)–hydrogen atoms.

Synthesis and characterization of six-membered pincer nickelacycles and application in alkylation of benzothiazole