Cu(I)-azidopyrrolo[3,2-d]pyrimidine Catalyzed Glaser-Hay Reaction under Mild Conditions.

ABSTRACT: The limitation of the CuAAC "click" reaction with a 2-azidopyridine substrate, owing to its equilibrium with a tetrazole isomer, is exploited herein for its utility in the Glaser-Hay reaction. A catalytic combination of a 2-azidopyridine analogue, 4-azido-5H-pyrrolo[3,2-d]pyrimidine, and CuI afforded homocoupled products of terminal alkynes, without any trace of triazole product, under mild conditions with a broad substrate scope. Emphasis on carbohydrate-based substrates appended to a propargylic group led to 1,3-diynes in good to excellent yields.

SUBMITTER: Thangarasu AK 

PROVIDER: S-EPMC9954286 | biostudies-literature | 2022 Feb

REPOSITORIES: biostudies-literature