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Three‐Component α‐Thienylation/Oxylation Cascade of I<sup>III</sup>/S<sup>VI</sup>‐Ylides via Photoinduced EDA Complex Activation

Zhiyun Du, Li Li, Zhaofeng Wang

2025European Journal of Organic Chemistry6 citationsDOIOpen Access PDF

Abstract

Abstract Herein, a visible‐light‐induced three‐component cascade of α ‐thienylation/oxylation of I III /S VI ‐ylides, substituted thiophenes and alcohols is reported. The core of the strategy involves electron‐donor‐acceptor (EDA) complex formation between I III /S VI ‐ylides and electron‐rich thiophenes. Upon photo‐activation, I III /S VI ‐ylides in‐situ generates sulfoxonium ylide radical, which is trapped by thiophenes to generate α ‐thienyl‐ α’ ‐ketyl sulfoxonium ylides and initiated subsequent carbenic O−H insertion from alcohol component. All reactions are operationally simple and proceed smoothly under mild reaction conditions, affording a broad range of unsymmetrical α,α‐disubstituted ketones in moderate to good yields.

Topics & Concepts

ChemistryCascadeComponent (thermodynamics)StereochemistryCombinatorial chemistryThermodynamicsChromatographyPhysicsSynthesis and Catalytic ReactionsOrganic Chemistry Cycloaddition ReactionsSulfur-Based Synthesis Techniques
Three‐Component α‐Thienylation/Oxylation Cascade of I<sup>III</sup>/S<sup>VI</sup>‐Ylides via Photoinduced EDA Complex Activation | Litcius