March 3, 2026

Photocatalytic Divergent Trifluoromethylthiolation of N ‐Sulfonylacrylamides Enabling Access to SCF 3 ‐Substituted Alkenes and Oxindoles

Key Points

This approach yields vinyl trifluoromethylthioethers and trifluoromethylthiolated oxindoles efficiently by varying conditions.
Utilizing the metal and oxidant-free photocatalytic method, the protocol provides broad applications in organic synthesis.
The transformation demonstrates significant advantages in accessing valuable trifluoromethylthiolated molecules from simple starting materials.
The protocol's mild conditions indicate potential for wider synthetic applications, although optimization may be necessary for some substrates.

Abstract

The divergent construction of molecules with a trifluoromethylthio group addresses significant synthetic challenges and is highly desirable in organic chemistry. Herein, we report a photocatalytic, metal and oxidant‐free, practical, and efficient strategies for divergent trifluoromethylthiolation of N ‐sulfonylacrylamides to the synthesis of synthetically useful vinyl trifluoromethylthioethers (via Heck coupling) and trifluoromethylthiolated oxindoles (via Smiles rearrangement). This divergent transformation occurred smoothly, driven by different reaction conditions, enabling achievement of Heck coupling and cascade rearrangement reactions, respectively. This protocol provides a mild and efficient strategy to access synthetically valuable trifluoromethylthiolated molecules from readily available chemicals.

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Photocatalytic Divergent Trifluoromethylthiolation of N ‐Sulfonylacrylamides Enabling Access to SCF 3 ‐Substituted Alkenes and Oxindoles

Key Points

Abstract

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