Cu(I)-Bis(phosphine) Dioxides as Catalysts for the Enantioselective α-Arylation of Carbonyl Compounds

The transition-metal-catalyzed alpha-arylation of carbonyl compounds was first reported by Buchwald and Hartwig in 1997. This transformation has been used and studied extensively over the last two decades. Enantioselective variants were also developed that allow for controlling the product stereochemistry. However, these suffer several limitations in the context of formation of tertiary stereocenters. Presented here is our group's contribution to this research area. The chiral Cu-bis(phosphine) dioxides catalytic system that we reported allowed accessing the enantioselective alpha-arylation of ketones that were not suitable for this transformation before in good yields and er up to 97.5:2.5. Preliminary insight and speculation concerning the reaction mechanism involving the unusual pairing of bis(phosphine) dioxides with transition-metal catalysts is also given.

Automated summary

The paragraph discusses the development of transition-metal-catalyzed alpha-arylation of carbonyl compounds, including enantioselective variants. It also mentions a new chiral Cu-bis(phosphine) dioxides catalytic system for selective alpha-arylation of ketones. Preliminary insight into the unusual pairing of bis(phosphine) dioxides with transition-metal catalysts in the reaction mechanism is also provided.