Journal
ACS CATALYSIS
Volume 10, Issue 15, Pages 8315-8320Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.0c02950
Keywords
nickel-catalysis; decarbonylation; fluoroalkyl carboxylic acids; thioether synthesis; fluoroalkylation
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Funding
- NIH NIGMS [GM073836, GM136332]
- Danish National Research Foundation (Carbon Dioxide Activation Center
- CADIAC)
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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 (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 (RFSR), with R = both aryl and alkyl.
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