Dong Group at UChicago

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  Dong Group at UChicago gbdlab.bsky.social · Jun 12, 2025
  How do you turn a carbonyl into sulfur? In this work, Zining from our lab developed a carbonyl-to-sulfur swap enabled by a rationally designed N′-alkyl-hydrazonamide (NAHA) reagent that promotes double C-C bond activation. www.science.org/doi/10.1126/...
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  Jake Yeston jakeyeston.bsky.social · Jun 12, 2025
  Out First Release in @science.org today, Zining Zhang in @donglab.bsky.social swaps out ketones for sulfur in saturated carbon rings through two modes of radical trapping www.science.org/doi/10.1126/...
  

  Carbonyl-to-sulfur swap enabled by sequential double carbon-carbon bond activation

  In drug development, replacement of a skeletal carbon with a sulfur atom can result in analogs of bioactive compounds with improved properties. Currently, the sulfur analogs are almost exclusively pre...

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  Dong Group at UChicago gbdlab.bsky.social · Jun 3, 2025
  So excited to share a new achievement by Zining and Kezhi in collaboration with Prof. Peng Liu!!! We developed a Cu-mediated deacylative fluorination approach that can convert a wide range of methyl ketones to the corresponding alkyl fluorides. pubs.acs.org/doi/full/10....
  

  Alkyl Fluoride Synthesis via Cu-Mediated Deacetylative Fluorination

  Given the increasing demand for diverse alkyl fluorides for various applications, it would be beneficial to enrich the fluorination toolbox by including more kinds of common functional groups, such as ketones, as fluoride surrogates. Here we report a Cu-mediated deacylative fluorination approach that can convert a wide range of methyl ketones to the corresponding alkyl fluorides. The reaction is enabled by a ketone activation reagent and a nucleophilic fluoride source. It features broad functional group tolerance, capability for the late-stage fluorination, fluoro-annulation, synthesis of α,α-dideuterated fluorides, and degree-controlled synthesis of mono-, di-, and trifluoro alkanes from a single ketone starting material. The computational studies suggest interesting Cu(III)-mediated C–F bond forming pathways via either fluorine atom transfer or an SN2 process.

  pubs.acs.org
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