What question did this study set out to answer?

The research aims to develop a catalyst-free method to synthesize (Z)-β-chloroenamines from alkenyl thianthrenium salts.

February 28, 2026

Base-promoted cascade haloamination/β-elimination of alkenyl thianthrenium salts: access to ( Z )-β-chloroenamines

Puntos clave

The research aims to develop a catalyst-free method to synthesize (Z)-β-chloroenamines from alkenyl thianthrenium salts.
Base-promoted cascade chloramination and β-elimination
Utilization of alkenyl thianthrenium salts and N-chlorosulfonamides
No catalysts or oxidants required
Successful synthesis of (Z)-β-chloroenamine products
Mild reaction conditions with good functional group compatibility
High stereoselectivity and excellent atom economy

Resumen

(Z)-β-Halo-enamines are widely found in natural products and drugs and are used in organic synthesis. However, accessing these molecules requires nucleophilic hydroaminations of 1-haloalkynes with amines. Herein, we report a catalyst-free, oxidant-free, base-promoted cascade chloramination/β-elimination of alkenyl thianthrenium salts with N-chlorosulfonamides, yielding (Z)-β-chloro-enamine products via π-π interactions. This reaction features mild reaction conditions, good functional group compatibility, excellent stereoselectivity, and high atom economy.

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