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Synfacts 2024; 20(03): 0285
DOI: 10.1055/s-0043-1773074
Polymer-Supported Synthesis

Intramicellar Pd-Catalyzed β-Arylation of Thiophenes

Contributor(s):
Yasuhiro Uozumi
,
Shintaro Okumura
Hauk P, Mazan V, Gallou F, *, Wencel-Delord J. * Université de Strasbourg, France and Novartis Pharma AG, Basel, Switzerland
Micellar Catalysis: A Green Solution to Enable Undirected and Mild C–H Activation of (Oligo)thiophenes at the Challenging β-Position.

Chem. Sci. 2023;
14: 12049-12055
DOI: 10.1039/d3sc03708h.
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Key words

micelle - palladium catalysis - thiophenes - C–H arylation

Significance

Palladium-catalyzed C–H arylation of thiophenes with aryl iodides was found to proceed with ‘unusual’ β-position selectivity in the presence of a proline-based surfactant PS-750-M. The arylation of a wide variety of (oligo)thiophenes was carried out with 10 mol% of Pd(OAc)2 in a three wt% aqueous solution of PS-750-M in the presence of silver acetate and undecanoic acid at room temperature to give the corresponding β-arylated thiophenes with excellent regioselectivity.


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Comment

The amphiphilic proline-based surfactant PS-750-M formed micelles in situ under the reaction conditions. The authors proposed that the arylation took place inside the micelles. Undecanoic acid significantly accelerate the arylation. The arylation did not proceed in the absence of silver acetate.


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Publication History

Article published online:
14 February 2024

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