Selective synthesis of alkyl amines and N-vinylazoles from vinyl sulfonium salts with N-nucleophiles?

Organic Chemistry Frontiers Pub Date: 2022-04-19 DOI: 10.1039/D2QO00434H

Abstract

Herein, we have developed an efficient and green method for the synthesis of various alkyl amines via the C(sp3)–S bond cleavage of vinylsulfonium salts. The reaction proceeds under air atmosphere with a broad scope of N-nucleophiles ranging from primary and secondary alkyl and aryl amines to various N-containing heterocycles. Moreover, in the presence of a base, the reaction of vinylsulfonium salts with N-containing heterocycles at room temperature can also afford N-vinylazoles with moderate to good yields. Finally, the practicality of this protocol is demonstrated by one-pot reaction, scale-up reaction and product derivatization.

Graphical abstract: Selective synthesis of alkyl amines and N-vinylazoles from vinyl sulfonium salts with N-nucleophiles
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