Taming highly unstable radical anions and 1,4-organodilithiums by flow microreactors: controlled reductive dimerization of styrenes

16 June 2022, Version 2
This content is a preprint and has not undergone peer review at the time of posting.


Reduction of styrenes with lithium arenide in a flow microreactor leads to the instantaneous generation of the radical anion of styrenes and subsequent dimerization by fast mixing to yield the corresponding 1,4-dilithium species. The efficiency and selectivity of this reductive dimerization are low in a batch reactor. A series of styrenes undergo the dimerization and the resulting 1,4-dilithium species are trapped with various electrophiles. Trapping with divalent electrophiles such as dichlorosilanes affords precursors for useful yet less accessible cyclic structures such as siloles. Single electron reduction of unsaturated compounds in flow microreactors has thus proved to be a powerful protocol in organic synthesis.


reductive dimerization
flow chemistry
radical anion

Supplementary materials

Supporting Information
Instrumentation and Chemicals, Preparation of Reagents and Substrates, Screening Conditions, Experimental Procedures, Characterization Data, Photophysical Properties, NMR Spectra


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