Nickel-Catalyzed Decarbonylative Synthesis of Fluoroalkyl
Thioethers
Posted on 2020-07-16 - 22:03
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
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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Brigham, Conor
E.; Malapit, Christian A.; Lalloo, Naish; Sanford, Melanie S. (2020). Nickel-Catalyzed Decarbonylative Synthesis of Fluoroalkyl
Thioethers. ACS Publications. Collection. https://doi.org/10.1021/acscatal.0c02950
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AUTHORS (4)
CB
Conor
E. Brigham
CM
Christian A. Malapit
NL
Naish Lalloo
MS
Melanie S. Sanford