Convergent Paired Electrosynthesis of β-Nitroalcohols Combining of Anodic Generation of Benzaldehydes and Cathodic Formation of Nitromethyl Anion via an Electrogenerated Base

Abstract

Convergent paired electrosynthesis of β-nitroalcohols using an undivided cell was successfully demonstrated by combining anodic generation of benzaldehydes from benzyl alcohols and cathodic formation of nitromethyl anion from nitromethane (CH₃NO₂) via an electrogenerated base (EGB). Linear sweep voltammetry measurements in 0.1 M Bu₄NBF₄/CH₃NO₂ and 0.1 M Bu₄PBF₄/CH₃NO₂ (M = mol L⁻¹), and the electrolysis in the absence of a substrate using a divided cell suggested that N-methylhydroxylamine (N-CH₃NHOH) may be formed as an EGB. Paired electrolysis of various benzyl alcohols was carried out to provide the corresponding β-nitroalcohols in moderate yields except for p-nitrobenzyl alcohol.