Rh(III)-Catalyzed Atroposelective C–H Selenylation of 1‑Aryl Isoquinolines

Rhodium(III)-catalyzed
atroposelective C–H selenylation
of 1-aryl isoquinolines has been achieved. The direct C–H selenylation
reaction between 1-aryl isoquinolines and 2-(phenylselanyl)isoindoline-1,3-dione
in the presence of the chiral SCpRh(III) complex afforded a series
of axially chiral 1-aryl isoquinoline selenides in up to 95% yield
and 96% ee. The reaction features mild conditions and a broad substrate
scope. DFT calculations revealed that the C–Se bond formation
step proceeds through a formal SN2 pathway.