Convergent Paired Electrolysis for the Three‐Component Synthesis of Protected Homoallylic Alcohols

Synthetic Organic Electrochemical Methods Since 2000: On the Verge of a Renaissance

“…For example, Hilt and co-workers reported an electrochemical carbonyl allylation in DMF (Figure 52B). 905 The cathodic Barbier reaction was combined with the Shono oxidation of DMF at the anode. The allyl alcohol produced in the cathodic process was swiftly converted into the corresponding N , O -acetal, thwarting undesired alcohol oxidation.…”

Towards paired and coupled electrode reactions for clean organic microreactor electrosyntheses

“…Schematic presentation of a paired coupling process employing anodically generated radical cations and cathodically generated heterocyclic anions [46]. in N,N-dimethylformamide (DMF), and the formation of the corresponding three-component product was observed [48] ( Figure 13). Experimentally, it was observed that the best results for the paired electrolysis for the formation of such formamide-protected homoallylic alcohols were obtained when the allyl bromide/aldehyde ratio was 2:1.…”

“…Schematic presentation of the paired electrosynthesis of formamide-protected homoallylic alcohols[48].…”

Basic Strategies and Types of Applications in Organic Electrochemistry

“…Some time ago, we published the formation of a three‐component electrochemical convergent electrolysis in a quasi‐divided cell where the solvent was oxidized primarily at the anode to give the N ‐formyliminium ion reported also by other groups as primary oxidized intermediate (Scheme ) …”

“…Some time ago, we published the formation of a threecomponent electrochemical convergent electrolysis in a quasidivided cell where the solvent was oxidized primarily at the anode to give the N-formyliminium ion reported also by other groups as primary oxidized intermediate (Scheme 14). [20] On the cathode, allyl bromide was reduced to the corresponding allyl anion which reacted in situ with aldehydes, such as benzaldehyde to form a secondary nucleophile. Combination of the two species led to the formation of the N,O-acetal-type products in moderate yields.…”