Electroreductive Ring-Opening Carboxylation of Cycloketone Oxime Esters with Carbon Dioxide

• DOI: 10.1021/acs.joc.2c01816
• Publication Date: 2022-10-23T12:51:25Z
• Authors: Xiao-Fei Liu; Ke Zhang; Lin-Lin Wang; He Wang; Jian Huang; Xun-Ting Zhang; Xiao-Bing Lu; Wen-Zhen Zhang
• Keywords: 01 natural sciences; 0104 chemical sciences

Electroreductive ring-opening carboxylation of cycloketone oxime esters with atmospheric carbon dioxide is reported. This reaction proceeded under simple constant current conditions in an undivided cell using glassy carbon as the cathode and magnesium as the sacrificial anode, providing substituted γ- and δ-cyanocarboxylic acids in moderate to good yields. Electrochemically generated cyanoalkyl radicals and cyanoalkyl anion are proposed as the key intermediates.