Unveiling the Potential of SNS-Ni Complex for Establishing C–N Bonds: An Approach toward Chemoselectivity

Recent research has focused a lot on using the borrowing hydrogen (BH) approach to react amines with alcohols to convert a C–O bond into a C–N bond. However, the notion of chemoselectivity in BH-mediated N-alkylation of amines has rarely been studied. Herein, we have demonstrated the application of a synthesized SNS-Ni complex constructing various C–N bonds via the coupling of diverse amines with various alcohols. Delightfully, the catalytic protocol also activates challenging C4–C16 aliphatic alcohols. Aryl amino alcohols are selectively N-alkylated with different alcohols, while keeping the OH group intact in the amino alcohol portion. Furthermore, without reducing the distal unsaturation, the catalytic technique was also successfully employed for the chemoselective N-alkylation of different fatty alcohols. The preliminary mechanistic investigation suggests alkylation occurs via a nonradical borrowing hydrogen pathway.