Stereoselective Synthesis of ( <i>E</i> )‐1,2‐Diarylethene via Palladium‐Catalyzed Decarboxylative Cross‐Coupling of Phenylacrylic Acids with Aryl Halides: Access to Resveratrol, Pinosylvin, and Pterostilbene

A series of ( E )‐1,2‐diarylethenes were efficiently synthesized via a Pd‐catalyzed decarboxylative cross‐coupling of various phenylacrylic acids with diverse (hetero)aryl halides. This protocol afforded the corresponding trans ‐stilbene derivatives cross‐coupled products in high yields across numerous substrates (48 examples), exhibiting excellent tolerance toward sensitive functional groups, including heterocycles. Notably, a catalytic amount of silver salt was employed as a cocatalyst, replacing the stoichiometric quantities required in previous studies. A sequence of spectroscopic experiments, were performed to investigate and identify the catalytically active species’ oxidation state. The versatility of this methodology was demonstrated through the synthesis of resveratrol , pinosylvin , and pterostilbene, all known for their diverse biological activities. Additionally, the photophysical properties of selected synthesized products were investigated, revealing promising luminescent characteristics.

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Publication Details

Journal
European Journal of Organic Chemistry
Published
2026-06-18
DOI
https://doi.org/10.1002/ejoc.70625
Primary Topic
Sirtuins and Resveratrol in Medicine
Type
article
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article

Stereoselective Synthesis of ( E )‐1,2‐Diarylethene via Palladium‐Catalyzed Decarboxylative Cross‐Coupling of Phenylacrylic Acids with Aryl Halides: Access to Resveratrol, Pinosylvin, and Pterostilbene

Parna Pramanik, Laksmikanta Adak, Ujjal Bhattacharjee, Shreyasi Chakraborty et al.
European Journal of Organic Chemistry
Sirtuins and Resveratrol in Medicine
article

Stereoselective Synthesis of ( E )‐1,2‐Diarylethene via Palladium‐Catalyzed Decarboxylative Cross‐Coupling of Phenylacrylic Acids with Aryl Halides: Access to Resveratrol, Pinosylvin, and Pterostilbene

Parna Pramanik, Laksmikanta Adak, Ujjal Bhattacharjee, Shreyasi Chakraborty, Rahul Mondal, Suprakash Sahoo, Piu Das
article en

Abstract

A series of ( E )‐1,2‐diarylethenes were efficiently synthesized via a Pd‐catalyzed decarboxylative cross‐coupling of various phenylacrylic acids with diverse (hetero)aryl halides. This protocol afforded the corresponding trans ‐stilbene derivatives cross‐coupled products in high yields across numerous substrates (48 examples), exhibiting excellent tolerance toward sensitive functional groups, including heterocycles. Notably, a catalytic amount of silver salt was employed as a cocatalyst, replacing the stoichiometric quantities required in previous studies. A sequence of spectroscopic experiments, were performed to investigate and identify the catalytically active species’ oxidation state. The versatility of this methodology was demonstrated through the synthesis of resveratrol , pinosylvin , and pterostilbene, all known for their diverse biological activities. Additionally, the photophysical properties of selected synthesized products were investigated, revealing promising luminescent characteristics.

European Journal of Organic Chemistry
Indian Institute of Technology Kharagpur (IN), Indian Institute of Engineering Science and Technology, Shibpur (IN)
Openalex Percentile: Top 8%
Sirtuins and Resveratrol in Medicine
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Stereoselective Synthesis of ( <i>E</i> )‐1,2‐Diarylethene via Palladium‐Catalyzed Decarboxylative Cross‐Coupling of Phenylacrylic Acids with Aryl Halides: Access to Resveratrol, Pinosylvin, and Pterostilbene — Parna Pramanik, Laksmikanta Adak, et al. · European Journal of Organic Chemistry (2026) | TGRS Research Map | TGRS