One-Pot Synthesis of Bio-based Styrenes from β-(Phenyl)-β-(phenyl­thio)propionic Acids via Neutral Ionic Liquid, Microwave Irradiation Triggered Cascade Decarboxylative Dehydrosulfenylation

Abstract

A direct, new and eco-friendly strategy for the one-step synthesis of methoxylated and hydroxylated styrenes from β-(phenyl)-β-(phenylthio)propionic acids is reported. This approach utilizes a neutral ionic liquid [hmim]Br-triggered cascade decarboxylative dehydrosulfenylation reaction under microwave irradiation, without the need for strong bases, acids and toxic metal oxidants, and eliminates the need for a phenolic group protection–deprotection strategy, thus offering an efficient route to bio-based commercially important FEMA GRAS approved vinylphenols. NMR studies suggest a concerted reaction mechanism.

Key words

ionic liquids - microwave irradiation - deprotected - decarboxylative dehydrosulfenylation - styrenes

Publication History

Received: 23 November 2024

Accepted after revision: 29 January 2025

Accepted Manuscript online:
29 January 2025

Article published online:
05 March 2025

• References

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