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Updated: Aug 1, 2025
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Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
Published on: July 17, 2020
Thiochromane Formation via Visible-Light-Mediated Intramolecular δ-C(sp3)-H Bond Arylation of Sulfonamides
Shuai Liu1, Nivesh Kumar1, Frédéric Robert1
1University of Bordeaux, CNRS, Bordeaux INP, ISM, UMR 5255, F-33400 Talence, France.
Abstract:
Visible-light-mediated intramolecular site-selective δ-C(sp3)-H bond arylation of aliphatic trifluoromethanesulfonamides was developed. The reaction proceeds through a radical cascade, including the generation of a sulfonamidyl radical, which triggers a 1,5-hydrogen atom transfer, affording a δ-C-centered radical, which finally cyclized onto a neighboring thiopolyfluoroaryl moiety to deliver a range of synthetically useful thiochromanes. The cyclization process occurs through two distinct pathways depending upon the nature of the substituent X ortho to the native C-S bond.
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