Fig. 4: Mechanistic investigations and proposed electrochemical cycloaddition mechanism. | Nature Communications

Fig. 4: Mechanistic investigations and proposed electrochemical cycloaddition mechanism.

From: Electrochemical and photocatalytic generation of cis-olefin-bridged carbodication for umpolung [4+1] cycloaddition

Fig. 4: Mechanistic investigations and proposed electrochemical cycloaddition mechanism.The alternative text for this image may have been generated using AI.

a Effect of HFIP on oxidation potentials of aniline in DCM and DCM/HFIP. b Effect of HFIP on oxidation potentials of 1a in DCM and DCM/HFIP. c Measurement of the real-time anodic potentials under standard electrolysis conditions using an Ag/AgNO3 reference electrode. d Generation of dication species 1a2+ and its redox property under standard electrolysis conditions in a divided cell. e Cycloaddition of 1a2+ with PhNH2 under current-free conditions. f Proposed electrochemical cycloaddition mechanism. g Theoretical study of transition states for the intermolecular nucleophilic addition of aniline to the cis-dication. h Theoretical study of transition states for the intramolecular nucleophilic addition. Calculations were performed at the SMD(HFIP)/M06-2X/def2-SVP level. 1H NMR yields are shown using CH2Br2 as an internal standard.

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