ArticleJACS Au2022
Taming Highly Unstable Radical Anions and 1,4-Organodilithiums by Flow Microreactors: Controlled Reductive Dimerization of Styrenes.
Article in JACS Au, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 4 papers.
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Who cites it
4 citing papers in PubMed.
- Real-Time Visualization of Turbulent Micromixing in a T-Mixer: Submillisecond Homogenization Revealed by Chemiluminescence.Analytical chemistry · 2026Article
- Electrolyte-Guided Selectivity Unlocks Pathway Control in Electrochemical Olefin Functionalization.Journal of the American Chemical Society · 2026Article
- Reductive Head-to-Head Coupling of Phenylacetylenes in the Coordination Sphere of an Osmium-Polyhydride.Organometallics · 2025Article
- Continuous flow synthesis enabling reaction discovery.Chemical science · 2024Review
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Authors and funding
2 authors.
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Abstract
The reduction of styrenes with lithium arenide in a flow microreactor leads to the instantaneous generation of highly unstable radical anions that subsequently dimerize to yield the corresponding 1,4-organodilithiums. A flow reactor with fast mixing is essential for this reductive dimerization as the efficiency and selectivity are low under batch conditions. A series of styrenes undergo dimerization, and the resulting 1,4-organodilithiums are trapped with various electrophiles. Trapping with divalent electrophiles affords precursors for useful yet less accessible cyclic structures, for example, siloles from dichlorosilanes. Thus, we highlight the power of single-electron reduction of unsaturated compounds in flow microreactors for organic synthesis.
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