Volume 2022, Issue 25 e202200288
Research Article

Palladium-Catalyzed Direct C−H Olefination of Polyfluoroarenes with Alkenyl Tosylates

Ka Yee Yee

Ka Yee Yee

Department of Chemistry and State Key Laboratory of Synthetic Chemistry, The Chinese University of Hong Kong, Shatin, New Territories, Hong Kong, China

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Dr. Man Pan Leung

Dr. Man Pan Leung

Department of Chemistry and State Key Laboratory of Synthetic Chemistry, The Chinese University of Hong Kong, Shatin, New Territories, Hong Kong, China

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Man Ho Tse

Man Ho Tse

Department of Chemistry and State Key Laboratory of Synthetic Chemistry, The Chinese University of Hong Kong, Shatin, New Territories, Hong Kong, China

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Dr. Pui Ying Choy

Dr. Pui Ying Choy

Department of Chemistry and State Key Laboratory of Synthetic Chemistry, The Chinese University of Hong Kong, Shatin, New Territories, Hong Kong, China

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Prof. Dr. Fuk Yee Kwong

Corresponding Author

Prof. Dr. Fuk Yee Kwong

Department of Chemistry and State Key Laboratory of Synthetic Chemistry, The Chinese University of Hong Kong, Shatin, New Territories, Hong Kong, China

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First published: 15 June 2022
Citations: 1

Graphical Abstract

A new indolylphosphine ligand L1 has been developed for the palladium-catalyzed direct C−H olefination of polyfluoroarenes with moisture and thermal stable alkenyl tosylates. The catalyst system employing L1 was found to be effective in this reaction with good structural and functional compatibility.

Abstract

The first general examples of palladium-catalyzed direct C−H olefination of polyfluoroarenes using alkenyl tosylates as electrophilic coupling partners are presented. By employing the Pd/L1 catalyst system (L1=N-methyl-2-(2’,4’-dimethoxyphenyl)-3-dicyclohexylphosphinoindole), the olefinated polyfluoroarenes can be obtained in good-to-excellent yields. Good structural and functional compatibility are also exhibited. In particular, the steric demanding and heterocyclic alkenyl tosylates react smoothly under this catalyst system. This reaction can be practicably performed on a gram-scale without significantly loss of product yields.

Conflict of interest

The authors declare no conflict of interest.

Data Availability Statement

The data that support the findings of this study are available in the supplementary material of this article.