Organic electrosynthesis using toluates as simple and versatile radical precursors

The electrolysis of toluateesters leads smoothly to the formation of the radical of the alkyl fragment. This property has been used to develop a new electrochemical deoxygenation reaction

Electrochemical methoxymethylation of alcohols – a new, green and safe approach for the preparation of MOM ethers and other acetals

A new, green, safe, cost-effective and highly efficient electrochemical approach for the methoxymethylation of alcohols and phenols was successfully developed. The methodology was also applied to the synthesis of substituted acetals

Synthesis of diketones, ketoesters and tetraketones by electrochemical oxidative decarboxylation of malonic acid derivatives: Application to the synthesis of cis-jasmone

Disubstituted malonic acid derivatives are smoothly converted into diketones and ketoesters in good to excellent yield (68% to 91%) under electrochemical conditions. The scope can be extended to transform trisubstituted bis-malonic acids into tetraketones in 77% to 86% yield. The new method was applied to the total synthesis of cis-jasmone

Electrochemical deoxygenation of primary alcohols

Direct electrolysis of primary alcohols, in the presence of methyl toluate, leads smoothly to the formation of the corresponding deoxygenated product in high yield

Novel electrochemical deoxygenation reaction using diphenylphosphinates

The electrochemical reduction of diphenylphosphinate esters leads smoothly and in high yields to the corresponding deoxygenated products. In comparison with the previously developed methodologies, the electrolysis could be performed at lower temperature and with a higher current density, resulting in a shorter reaction time

Toluates: unexpectedly versatile reagents

The mechanism of the monoelectronic reduction of aromatic esters has been investigated. The unexpected synthetic utility of the toluate moiety in the deoxygenation of alcohols and the allylation of ketones is also reported. Finally, the use of aromatic esters as robust, though easily removable, protecting groups is depicted. © 2009 Elsevier Ltd. All rights reserved

Short, asymmetric synthesis of epi-morphine ACNO analogues

A concise and efficient asymmetric synthesis of ACNO analogues of morphine is reported