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Visible-Light-Induced Tertiary C(sp<sup>3</sup>)–H Sulfonylation: An Approach to Tertiary Sulfones

Sumedha Swarnkar, Mohd Yeshab Ansari, Atul Kumar

2021Organic Letters18 citationsDOI

Abstract

In seeking to broaden the lexicon of photocatalysis and considering the importance of sulfones as essential pharmaceuticals, herein one-pot visible-light-induced tertiary C(sp3)–H sulfonylation is explored for the first time using indoline-2,3-diones, 4-hydroxy proline, and sulfinic acids as model substrates in the presence of iodine and Na2-Eosin Y as a photocatalyst. In addition, this transformation unlocks a new strategy in the context of the late-stage tertiary C(sp3)–H sulfonylation of Monastrol, a selective Eg5 inhibitor, and its analogue.

Topics & Concepts

ChemistryIndolineContext (archaeology)Tertiary careSulfonylEosin YTertiary alcoholsPhotocatalysisIodineMedicinal chemistryCombinatorial chemistryOrganic chemistryCatalysisFamily medicinePaleontologyBiologyMedicineAlkylSulfur-Based Synthesis TechniquesRadical Photochemical ReactionsCatalytic C–H Functionalization Methods
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