Convergent Paired Electrosynthesis of β-Nitroalcohols Combining 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 (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.

Keywords

• paired electrosynthesis
• electrogenerated base
• henry reaction
• β-nitroalcohol