Catalytic Reduction of Sulfoxides in Organic Synthesis

The catalytic reduction of sulfoxides to sulfides represents a cornerstone transformation in modern organic synthesis, offering both functional group interconversion and access to valuable organosulfur scaffolds. Strategies span metal‐based and metal‐free systems, photocatalytic and electrochemical routes, and solvent‐intensive or solvent‐free protocols. Mechanistic paradigms include hydride transfer, single‐electron transfer with radical chain propagation, and nucleophilic attack on activated sulfoxide intermediates. Advances in catalyst design have improved selectivity and broadened substrate scope, permitting the reduction of sterically hindered or functionalised sulfoxides under mild conditions. The combination of visible‐light activation and earth‐abundant catalysts underscores a shift towards sustainable redox processes. Industrial relevance is manifest in the scalable deoxygenation of sulfoxide motifs within pharmaceutical intermediates, agrochemicals and materials precursors, aligning with green chemistry principles by minimising hazardous waste and energy consumption.

Research from Nature Portfolio

No recent Nature Portfolio content available.

Catalytic Reduction of Sulfoxides in Organic Synthesis publication trend

The graph below shows the total number of articles in catalytic reduction of sulfoxides in organic synthesis across all publications each year (not limited to Nature Index journals).

Technical terms

Sulfoxide: an organosulfur compound featuring a sulfur atom bonded to two carbon groups and one oxygen atom, serving as the oxidation‐state +IV precursor to sulfides.

Sulfide: an organosulfur species in which a sulfur atom bridges two carbon substituents, often the product of sulfoxide reduction.

Photoredox catalysis: catalytic strategy employing light‐absorbing catalysts to mediate single‐electron transfer events, enabling redox transformations under mild conditions.

Radical chain mechanism: a reaction pathway in which reactive radical intermediates propagate a sequence of bond‐breaking and bond‐forming steps to sustain the transformation.

Chlorosulfonium salt: an electrophilic intermediate formed by reaction of sulfoxides with chlorinating agents, facilitating nucleophilic reduction to sulfides.

References

1. Photocatalytic Deoxygenation of Sulfoxides Using Visible Light: Mechanistic Investigations and Synthetic Applications. ACS Catalysis (2020).
2. NaSH-HCl mediated reduction of sulfoxides into sulfides under organic solvent-free reaction conditions. Green Chemistry Letters and Reviews (2020).
3. Reduction of Sulfoxides in Multigram Scale, an Alternative to the Use of Chlorinated Solvents. Processes (2022).