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Jul 19 2018


The copper(I)-doped zeolite CuI−USY proved to be a versatile, efficient, and recyclable catalyst for various Ullmann-type coupling reactions. Easy to prepare and cheap, this catalytic material enables the arylation and heteroarylation of diverse O-, N-, S-, and C-nucleophiles under ligand-free conditions while exhibiting large functional group compatibility. The facility of this catalyst to promote C−O bond formation was further demonstrated with the total synthesis of 3-methylobovatol, a naturally occurring diaryl ether of biological relevance. From a mechanistic viewpoint, two competitive pathways depending on the nature of the nucleophile and consistent with the obtained results have been proposed.  

Graphical Abstract:

graphical abstract

Reference :

Tony Garnier, Mathieu Danel, Valentin Magné, Anthony Pujol, Valérie Bénéteau, Patrick Pale, and Stefan Chassaing

Copper(I)−USY as a Ligand-Free and Recyclable Catalyst for Ullmann-Type O‐, N‐, S‐, and C‐Arylation Reactions: Scope and Application to Total Synthesis

J. Org. Chem., 83 (12), 6408-6422, DOI: 10.1021/acs.joc.8b00620

Contact chercheur :

Stefan Chassaing (courriel : chassaing@unistra.fr) and Patrick Pale (courriel : ppale@unistra.fr), LASYROC, Institut de Chimie (UMR 7177).