Asymmetric Alkyl and Aryl/Azolation of Alkenes via a Single Cu(I) Complex

The copper-catalyzed, highly enantioselective alkyl and aryl/azolation of alkenes is reported. The employment of the chiral carbazole-based bisoxazoline (Cbzbox) ligand is critical to the success of this chemistry. Anionic tridentate ligands improve the reducibility of copper complexes, facilitating alkyl/aryl radical generation and providing good enantiocontrol in the azolation. The three-component coupling reactions feature mild reaction conditions and tolerate broad range of functional groups. This strategy allows straightforward introduction of valuable azole functionalities into a elaborated molecular system through direct C-H functionalization.

Automated summary

This study describes a copper-catalyzed, highly enantioselective alkyl and aryl/azolation of alkenes, where the use of a specific chiral ligand plays a crucial role in the success of the chemistry. Anionic tridentate ligands are employed to enhance the reducibility of copper complexes, facilitating the generation of alkyl/aryl radicals and providing good enantiocontrol in the azolation. The three-component coupling reactions have mild reaction conditions and can tolerate a broad range of functional groups, allowing for the straightforward introduction of valuable azole functionalities into complex molecular systems through direct C-H functionalization.