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Beilstein J. Org. Chem. 2018, 14, 891–899, doi:10.3762/bjoc.14.76
Graphical Abstract
Scheme 1: The Corey–Fuchs reaction.
Scheme 2: Electrochemical reduction of a carbon–halogen bond.
Scheme 3: Electrochemical synthesis of vinyl bromides [25].
Scheme 4: Scope of this work.
Figure 1: Voltammetric curves of 1a 0.020 mol dm−3; Pt, glassy carbon (GC) or Ag cathode. ν = 0.2 V s−1, T = ...
Scheme 5: Possible products from the electrolysis of 2-(2,2-dibromovinyl)naphthalene (1a).
Figure 2: Variation of the amounts of 1a, 2a, and 3a with the number of Faradays of 1a.
Scheme 6: Mechanistic hypothesis for the synthesis of alkyne 2a and bromoalkyne 3a from 2-(2,2-dibromovinyl)n...
Scheme 7: Possible reaction using NaClO4 as supporting electrolyte.
Scheme 8: Electrochemical synthesis of 9-ethyl-3-ethynyl-9H-carbazole (2b).
Scheme 9: Electrochemical synthesis of 1-ethynyl-4-methoxybenzene (2c).