Streptocyanine as an activation mode of amine catalysis for the conversion of pyridine rings to benzene rings.

ABSTRACT: Amine catalysts have emerged as an invaluable tool in organic synthesis. Iminium, enamine, and enamine radical cation species are representative activation modes of amine catalysis. However, the development of new amine catalysis activation modes that enable novel synthetic strategies remains highly desirable. Herein, we report streptocyanine as a new amine catalysis activation mode, which enables the skeletal editing of pyridine rings to benzene rings. N-Arylation of pyridines bearing an alkenyl substituent at the 3-position generates the corresponding N-arylpyridiniums. The resulting pyridinum reacts with a catalytic amount of piperidine to afford a streptocyanine intermediate. Catalytically generated streptocyanine forms a benzene ring via a ring-closing reaction, t

SUBMITTER: Morofuji T 

PROVIDER: S-EPMC9847661 | biostudies-literature | 2023 Jan

REPOSITORIES: biostudies-literature