2020 journal article

Nickel-Catalyzed Decarbonylative Synthesis of Fluoroalkyl Thioethers

ACS Catalysis, 10(15), 8315–8320.

By: C. Brigham*, C. Malapit *, N. Lalloo*  & M. Sanford *

author keywords: nickel-catalysis; decarbonylation; fluoroalkyl carboxylic acids; thioether synthesis; fluoroalkylation
UN Sustainable Development Goal Categories
6. Clean Water and Sanitation (OpenAlex)
Source: Crossref
Added: August 29, 2022

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.