Enantioselective C-H Alkenylation of Ferrocenes with Alkynes by Half-Sandwich Scandium Catalyst

The enantioselective C-H alkenylation of ferrocenes with alkynes is, in principle, a straightforward and atom-efficient route for the construction of planar-chiral ferrocene scaffolds bearing alkene functionality but has remained scarcely explored to date. Here we report for the first time the highly enantioselective C-H alkenylation of quinoline- and pyridine-substituted ferrocenes with alkynes by a half-sandwich scandium catalyst. This protocol features broad substrate scope, high enantioselectivity, and 100% atom efficiency, selectively affording a new family of planar-chiral ferrocenes bearing N/alkene functionalities. The mechanistic details have been clarified by DFT analyses. The use of a quinoline/alkene-functionalized ferrocene product as a chiral ligand for asymmetric catalysis is also demonstrated.

Automated summary

The study demonstrates the highly enantioselective C-H alkenylation of quinoline- and pyridine-substituted ferrocenes with alkynes using a half-sandwich scandium catalyst. This method offers broad substrate scope, high enantioselectivity, and selectively affords a new family of planar-chiral ferrocenes bearing N/alkene functionalities. The use of a quinoline/alkene-functionalized ferrocene product as a chiral ligand for asymmetric catalysis is also showcased.