Nickel-catalyzed deaminative Sonogashira coupling of alkylpyridinium salts enabled by NN2 pincer ligand

Alkynes are amongst the most valuable functional groups in organic chemistry and widely used in chemical biology, pharmacy, and materials science. However, the preparation of alkyl-substituted alkynes still remains elusive. Here, we show a nickel-catalyzed deaminative Sonogashira coupling of alkylpyridinium salts. Key to the success of this coupling is the development of an easily accessible and bench-stable amide-type pincer ligand. This ligand allows naturally abundant alkyl amines as alkylating agents in Sonogashira reactions, and produces diverse alkynes in excellent yields under mild conditions. Salient merits of this chemistry include broad substrate scope and functional group tolerance, gram-scale synthesis, one-pot transformation, versatile late-stage derivatizations as well as the use of inexpensive pre-catalyst and readily available substrates. The high efficiency and strong practicability bode well for the widespread applications of this strategy in constructing functional molecules, materials, and fine chemicals. Alkynes are amongst the most valuable functional groups in organic chemistry, however, the preparation of alkyl-substituted alkynes still remains elusive. Here the authors show a nickel-catalyzed deaminative Sonogashira coupling of alkylpyridinium salts.

Automated summary

This study presents a nickel-catalyzed deaminative Sonogashira coupling of alkylpyridinium salts to prepare alkyl-substituted alkynes efficiently. The development of a new easily accessible and bench-stable ligand enables alkyl amines to serve as alkylating agents in Sonogashira reactions with excellent yields.