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Catalytic Sulfone Upgrading Reaction with Alcohols via Ru(II)
preprintsubmitted on 27.12.2019, 08:40 and posted on 27.12.2019, 12:47 by Tomas Vojkovsky, Shubham Deolka, Saiyyna P. Stepanova, Michael C. Roy, Eugene Khaskin
Sulfones and sulfonamides with an α-CH bond can be easily alkylated by aliphatic alcohols to add the carbon skeleton of the alcohol via a one-step, Ru(II) catalyzed redox neutral reaction. The reaction requires a sub-stoichiometric amount of base and produces only water as a byproduct. A number of pharmaceutically relevant functional groups such as piperidine, morpholine, etc. are well tolerated under the reaction conditions to give higher value-added products in one step from widely available substrates. The reaction proceeds through a sulfone carbanion addition to an in-situ generated aldehyde formed via catalytic dehydrogenation and subsequent catalyst mediated replacement of the secondary alcohol by hydrogen.
Read the published paper
in ACS Catalysis