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Visible Light‐Mediated, Iodine‐Catalyzed Radical Cascade Sulfonylation/Cyclization for the Synthesis of Sulfone‐Containing Coumarin under Photocatalyst‐Free Conditions

Bing Yi, Qiang Wang, Jian‐Ping Tan, Ziqi Yi, Daiguang Li, Shiyuan Kang, wenhui zhang, Huan Tang, Yanjun Xie

2021Asian Journal of Organic Chemistry12 citationsDOI

Abstract

Abstract We have presented a visible‐light mediated, iodine catalyzed radical cascade sulfonylation/cyclization reaction by employing iodine as catalyst without addition of any of photocatalyst and oxidant. A number of sulfone‐containing coumarin derivatives with different substituent and functional groups were obtained in moderate to good yields. Besides, the practicality and utility of this protocol were demonstrated by the scale up synthesis. Furthermore, mechanistic investigations including control experiments and light on/off studies indicated that visible‐light irradiation and iodine catalyst were the essential elements to fulfill the radical cascade sulfonylation/cyclization process. This protocol featured green, economical and efficient, and opens a new opportunity for accessing to structurally diverse sulfone‐containing coumarin derivatives.

Topics & Concepts

ChemistrySulfonePhotoredox catalysisCoumarinCatalysisSubstituentPhotocatalysisVisible spectrumPhotochemistryCascade reactionCombinatorial chemistryIodineRadical cyclizationCascadeOrganic chemistryPhysicsChromatographyOptoelectronicsSulfur-Based Synthesis TechniquesRadical Photochemical ReactionsAdvanced Photocatalysis Techniques