Direct electrochemical α-cyanation of N-protected cyclic amines

Abstract

alpha-cyanation of N-protected cyclic amines was achieved using a direct electrochemical method. Unsubstituted N-protected cyclic amines were easily cyanated at the alpha-position using an undivided cell in high yields; moreover, alpha-cyanation of alpha'-substituted pyrrolidine and alpha'-,beta'- or gamma-substituted piperidines smoothly proceeded in high yield and with high to excellent diastereoselectivity. alpha-Substituted N-cyano-pyrrolidines and -piperidines were also cyanated at the more substituted position (the alpha-position) using a divided cell with high yield and high regioselectivity.

Electrochemistry of olanzapine and risperidone at carbon nanotubes modified gold electrode through classical and DFT approaches

“…4. The unstable iminium radical formed (6 or 7) can be easily oxidized to give the iminium cation which in turns decomposes by oxidation and hydrolysis on the ethylene bridge [46][47][48]. These reactions thus lead to the loss of reversibility of the electrochemical process, as actually experimentally observed.…”

Modern Electrochemical Aspects for the Synthesis of Value‐Added Organic Products

“…For example, the direct cyanation of a proline derivative at position 5 was reported (Scheme 39). 128 …”

Anodic Selective Functionalization of Cyclic Amine Derivatives

“…20 The regioselectivity was similar to the anodic methoxylation of N-protected cyclic amines. This anodic cyanation of L-proline derivative proceeded to afford 5-cis substituted product in excellent diastereoselectivity (Scheme 6).…”