This contribution reports the double Michael addition of primary, secondary and tertiary alcohols to divinyl sulfone and the optimization of the reaction conditions for this transformation. Optimization comprised the selection of the nitrogen or phosphorous based nucleophiles initiating the reaction and the reaction conditions (solvent choice, reaction temperature, stoichiometry, concentration, initiator loading). Preferable reaction conditions typically comprise a reaction temperature close to or below room temperature, high concentration of the reagents in dichloromethane as the solvent, which should be dry and a loading of 10 mol% triphenylphosphine. The speed of the reaction is then strongly dependent on the nature of the alcohol and increases in the order tertiary &lt; secondary &lt; primary alcohol as well as in the order aliphatic &lt; benzylic ≤ allylic &lt; propargylic alcohol. Finally, the prospect of this ol-ene reaction with respect to the well-established Thiol-ene “Click” reaction will be discussed.

Triphenylphosphine promoted hydroalkoxylation of divinyl sulfone: An ol-ene “Click” reaction?

249th National Meeting (2015)

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