Sulfilimines as Transformable and Retainable Directing Groups in Rhodium-Catalyzed ortho-C-H Bond Functionalization

Shown herein is the first time that the sulfilimine is utilized as a directing group for Rh(III)-catalyzed C-H activation/ annulation with intermolecular and intramolecular alkyne com-pounds. Sulfilimine serves as a transformable directing group, an internal oxidant, in the annulation with an alkyne moiety via N-S bond cleavage. Notably, the retention of sulfilimine as a directing group is also achieved in the Rh(III)-catalyzed ortho-alkynylation with alkyne bromides.

Automated summary

This study demonstrates for the first time the utilization of sulfilimine as a directing group for Rh(III)-catalyzed C-H activation/annulation with intermolecular and intramolecular alkyne compounds. Sulfilimine functions as a transformable directing group and an internal oxidant in the annulation with an alkyne moiety via N-S bond cleavage. Importantly, the retention of sulfilimine as a directing group is also achieved in the Rh(III)-catalyzed ortho-alkynylation with alkyne bromides.