Palladium-Catalyzed Reductive Conversion of Acyl Fluorides via Ligand-Controlled Decarbonylation

Yohei Ogiwara*, Yuka Sakurai, Hiroyuki Hattori and Norio Sakai*

*Department of Pure and Applied Chemistry, Faculty of Science and Technology, Tokyo University of Science, Noda, Chiba 278-8510, Japan, Email: yoheiogiwarars.tus.ac.jp, sakachemrs.noda.tus.ac.jp

Y. Ogiwara, Y. Sakuria, H. Hattori, N. Sakai, Org. Lett., 2018, 20, 4164-4167.

DOI: 10.1021/acs.orglett.8b01582

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Abstract

The combination of Pd(OAc)₂/Et₃SiH enables ligand-controlled non-decarbonylative and decarbonylative conversions of acyl fluorides. When tricyclohexylphosphine (PCy₂) was used as the ligand, aldehydes were obtained as simple reductive conversion products, whereas 1,2-bis(dicyclohexylphosphino)ethane (Cy₂P(CH₂)₂PCy₂, DCPE) as the ligand favored the formation of hydrocarbons as decarbonylative reduction products.

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Key Words

synthesis of aldehydes, decarboxylations, triethylsilane

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ID: J54-Y2018