Nickel-Catalyzed Cyanation of Unactivated Alkyl Sulfonates with Zn(CN)2.

Cyanation of unactivated primary and secondary alkyl mesylates with Zn(CN)2 catalyzed by nickel has been developed. The reaction provides an efficient route for the synthesis of alkyl nitriles with wide substrate scope, good functional group tolerance, and compatibility with heterocyclic compounds. Mechanistic studies indicate that alkyl iodide generated in situ serves as the reactive intermediate and the gradual release of alkyl iodide is crucial for the success of the reaction.

Citation

Aiyou Xia, Peizhuo Lv, Xin Xie, Yuanhong Liu. Nickel-Catalyzed Cyanation of Unactivated Alkyl Sulfonates with Zn(CN)2. Organic letters. 2020 Oct 16;22(20):7842-7847

PMID: 33006476

search → result