Cu/Pd-catalyzed C-2-H arylation of quinazolin-4(3H)-ones with (hetero)aryl halides

Julien Godeau (1) , Marine Harari (1) , Sylvain Laclef (1) , Emmanuel Deau (1) , Corinne Fruit (1) , Thierry Besson (1)

1 COBRA - Chimie Organique et Bioorganique : Réactivité et Analyse

The regiospecific C‐2–H arylation of N‐3‐substituted quinazolin‐4(3H)‐ones with a wide range of aryl or (hetero)aryl halides under microwave irradiation was studied. A ligand‐dependent palladium/copper bicatalytic system was developed and allowed direct cross‐coupling with a variety of (hetero)aryl halides. This useful and scalable procedure promotes the construction of C(sp2)–C(sp2) bonds from arenes or (hetero)arenes and aryl or (hetero)aryl bromides and chlorides in a time‐efficient strategy. The extension of the reaction to various N‐3‐substituted quinazolin‐4(3H)‐ones with iodobenzene as well as the scope and limitations of the method were also investigated.

Keywords: Nitrogen heterocycles; Microwave chemistry; C–H functionalization; Palladium; Cross‐coupling

Domains: Chemical Sciences

Julien Godeau, Marine Harari, Sylvain Laclef, Emmanuel Deau, Corinne Fruit, et al.. Cu/Pd-catalyzed C-2-H arylation of quinazolin-4(3H)-ones with (hetero)aryl halides. European Journal of Organic Chemistry, 2015, 2015 (35), pp.7705-7717. ⟨10.1002/ejoc.201501129⟩. ⟨hal-02046152⟩