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Nickel-Catalyzed Decarbonylative Synthesis of Fluoroalkyl Thioethers.

ABSTRACT: This report describes the development of a nickel-catalyzed decarbonylative reaction for the synthesis of fluoroalkyl thioethers (R_FSR) from the corresponding thioesters. Readily available, inexpensive, and stable fluoroalkyl carboxylic acids (R_FCO₂H) serve as the fluoroalkyl (R_F) source in this transformation. Stoichiometric organometallic studies reveal that R_F-S bond-forming reductive elimination is a challenging step in the catalytic cycle. This led to the identification of diphenylphosphinoferrocene as the optimal ligand for this transformation. Ultimately, this method was applied to the construction of diverse fluoroalkyl thioethers (R_FSR), with R = both aryl and alkyl.

SUBMITTER: Brigham CE

PROVIDER: S-EPMC8294461 | biostudies-literature | 2020 Aug

REPOSITORIES: biostudies-literature

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Nickel-Catalyzed Decarbonylative Synthesis of Fluoroalkyl Thioethers.

Brigham Conor E CE Malapit Christian A CA Lalloo Naish N Sanford Melanie S MS

ACS catalysis 20200717 15

This report describes the development of a nickel-catalyzed decarbonylative reaction for the synthesis of fluoroalkyl thioethers (RFSR) from the corresponding thioesters. Readily available, inexpensive, and stable fluoroalkyl carboxylic acids (RFCO2H) serve as the fluoroalkyl (RF) source in this transformation. Stoichiometric organometallic studies reveal that RF-S bond-forming reductive elimination is a challenging step in the catalytic cyc ...[more]

PMID: 34306801

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