Synthesis Of Β-hydroxysulfones Research Articles

Synthesis of β-hydroxysulfones through a copper(ii)-catalyzed multicomponent reaction with the insertion of sulfur dioxide

A copper(ii)-catalyzed aerobic oxidative reaction of arylhydrazines, DABCO·(SO2)2 and alkenes is reported. Diverse β-hydroxysulfones are generated in moderate to good yields through the hydroxysulfonylation of alkenes with the insertion of sulfur dioxide under mild conditions. In some cases, β-ketosulfones are produced.

Synthesis of β-Hydroxysulfones from Sulfonyl Chlorides and Alkenes Utilizing Visible Light Photocatalytic Sequences.

The synthesis of β-hydroxysulfones from sulfonyl chlorides and styrenes in the presence of water by a visible light mediated atom transfer radical addition (ATRA)-like process utilizing fac[Ir(ppy)3] as photoredox catalyst was developed in high yields. This process could be combined with the visible light mediated synthesis of trifluoromethylated sulfonyl chlorides via an ATRA reaction between alkenes and CF3SO2Cl utilizing [Cu(dap)2Cl] as photoredox catalyst, demonstrating the possibility of sequential photoredox processes.

ChemInform Abstract: Molecular‐Iodine‐Catalyzed Aerobic Oxidative Synthesis of β‐Hydroxy Sulfones from Alkenes.

The synthesis of β-hydroxy sulfones from alkenes and sodium sulfinates under aerobic oxidative conditions was achieved in the presence of a catalytic amount of molecular iodine. Molecular oxygen in air serves as the terminal oxidant and the catalytic amount of molecular iodine acts as the sulfonyl radical initiator and peroxide reductant.

An approach toward the synthesis of β-hydroxy sulfones on water

Various β-hydroxyl sulfones are prepared by regioselective ring opening of epoxides with sodium salt of sulfinate on water. This is an efficient protocol which avoids hazardous and moisture sensitive catalysts.

Synthesis of β-hydroxy sulfones via opening of hydrophilic epoxides with zinc sulfinates in aqueous media

Reaction of hydrophilic epoxides (ethylene oxide and propylene oxide) with readily accessible zinc sulfinates in aqueous solution under essentially neutral conditions afforded β-hydroxy sulfones in good yields. This method avoids the need for organic solvents and produces ZnO as the only major reaction byproduct. 2-(Methylsulfonyl)ethanol, a common reagent for the protection of various functional groups, was obtained by this methodology from ethylene oxide in 78% yield. Reaction of various simple zinc alkane- and benzenesulfinates with propylene oxide proceeded regioselectively in 63–67% yield. The corresponding opening of these epoxides with zinc 1,3-butadiene-1-sulfinate afforded 1-butadienyl β-hydroxyalkyl sulfones in 30% yield. Mechanistic studies revealed that the yields of these products were limited by their consumption in competing intra- and intermolecular Michael addition processes.