Nickel Complex Catalyzed Efficient Activation of sp3 and sp2 C–H Bonds for Alkylation and Arylation of Oxygen Containing Heterocyclic Molecules

Abstract

A nickel(II) complex (1) of N,N′-bis(2,6-diisopropylphenyl)-2,6-pyridinedicarboxamido (L) ligand was examined for catalytic coupling of Grignard reagents with the C–H bond of oxygen containing heterocyclic compounds such as tetrahydrofuran and furan. The nickel(II) complex showed excellent activity in catalyzing C–H activation and further coupling with various Grignard reagents. The effective activation of the C–H bond proceeded under ambient reaction conditions with a short reaction time (1–2 h). The catalyst (1) displays high turnover frequency of 4,130 h−1 with catalyst loading as low as 0.01 mol%. This catalytic route could prove to be an efficient mode of activation of sp3 and sp2 C–H bonds in various heterocycles for the preparation of synthetically and pharmaceutically relevant molecules.