Synthesis 2025; 57(10): 1762-1768
DOI: 10.1055/a-2528-5236
paper

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

Richa Singh
a   Medicinal & Process Chemistry Division, CSIR-Central Drug Research Institute, Sector 10, Jankipuram Extension, Sitapur Road, Lucknow U.P.-226031, India
b   Department of Chemistry, Gaya College, Gaya, Bihar 23001, India
,
Sumit K. Rastogi
a   Medicinal & Process Chemistry Division, CSIR-Central Drug Research Institute, Sector 10, Jankipuram Extension, Sitapur Road, Lucknow U.P.-226031, India
c   Academy of Scientific and Innovative Research, Ghaziabad, U.P.-110001, India
,
Santosh Kumar
a   Medicinal & Process Chemistry Division, CSIR-Central Drug Research Institute, Sector 10, Jankipuram Extension, Sitapur Road, Lucknow U.P.-226031, India
c   Academy of Scientific and Innovative Research, Ghaziabad, U.P.-110001, India
,
Danish Equbal
a   Medicinal & Process Chemistry Division, CSIR-Central Drug Research Institute, Sector 10, Jankipuram Extension, Sitapur Road, Lucknow U.P.-226031, India
,
Yogesh Thopate
a   Medicinal & Process Chemistry Division, CSIR-Central Drug Research Institute, Sector 10, Jankipuram Extension, Sitapur Road, Lucknow U.P.-226031, India
c   Academy of Scientific and Innovative Research, Ghaziabad, U.P.-110001, India
,
Arun K. Sinha
a   Medicinal & Process Chemistry Division, CSIR-Central Drug Research Institute, Sector 10, Jankipuram Extension, Sitapur Road, Lucknow U.P.-226031, India
c   Academy of Scientific and Innovative Research, Ghaziabad, U.P.-110001, India
› Author Affiliations


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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.

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Publication History

Received: 23 November 2024

Accepted after revision: 29 January 2025

Accepted Manuscript online:
29 January 2025

Article published online:
05 March 2025

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