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 compounds. Sulfilimine serves as a transformable directing group, an internal oxidant, in the annulation with an alkyne...

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Bibliographic Details
Published in:Organic letters 2022-09, Vol.24 (37), p.6772-6776
Main Authors: Liu, Jiechun, Jia, Xiaoyan, Huang, Liangbin
Format: Article
Language:English
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Summary: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 compounds. 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.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.2c02630