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

Abstract

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 S N 2 pathway.

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