Silver-Catalyzed Nitrogenation of Alkynes: A Direct Approach to Nitriles through C≡C Bond Cleavage

摘要

The transformation of alkynes is a fundamental method that has been widely used in organic synthesis. Alkyne chemistry can be dated back to the early nineteenth century. The hydration of alkynes to ketones(Scheme 1a) and the addition reactions of alkynes (Scheme 1 b) are early examples. Subsequently, various catalytic systems were developed. For example, the Pd-catalyzed Wacker-type oxidation to generate 1,2-diketones (Scheme 1c) is one of the most important industrial processes. The development of cycliza-tion reactions such as click chemistry (Scheme 1 d) has established new perspectives for the use of alkynes in drug discovery, materials science, supramolecular chemistry, polymer chemistry, and biotechnology. Furthermore, the coupling of terminal alkynes, such as the Sonogashira coupling (Scheme 1 e), provides important methods for C—C bond formation. The catalytic cleavage of C≡C bonds to produce carboxylic acids and new alkynes has also been disclosed (Scheme 1 f,g). Because of the significance and wide applications of such chemistry in organic synthesis, the exploration for new types of alkyne transformations is very attractive to researchers.