Synthesis of α,β-Unsaturated Carboxylic Acids by Nickel(II)-Catalyzed Electrochemical Carboxylation of Vinyl Bromides

Abstract

Electrochemical carboxylation of alkyl-substituted vinyl bromides (1a-1g) in the presence of 20 mol% of NiBr2•bpy under an atmospheric pressure of carbon dioxide with a platinum cathode and a magnesium anode gave the corresponding α,β-unsaturated carboxylic acids (2a-2g) in yields of 53-82%.

Electrocarboxylation of Acetophenone to 2‐Hydroxy‐2‐phenylpropionic Acid in the Presence of CO2

“…Through the protonation step, where a CO 2 molecule was lost, 4 reacted to form the aimed product 5. The Mg 2＋ from anodic oxidation dissolved in the electrolyte readily captured 5 to form stable magnesium carboxylate, 20 which gave 2-hydroxy-2-phenylpropionic acid after an acid treatment. Table 1.…”

Electrochemical fixation of CO2 to organohalides in room-temperature ionic liquids under supercritical CO2

“…In the electrochemical methods, highly reactive carbon nucleophiles are readily generated at cathodes and then react with CO 2 immediately to provide the corresponding carboxylated products. Over the past several decades, there have been many reports on the electrochemical fixation of CO 2 to various types of organic compounds such as organohalides [6][7][8][9][10][11][12][13][14][15][16], activated olefins [17][18][19], imines [20][21][22][23][24], and ketones [25][26][27][28] in conventional polar organic solvents. In addition, some of them focused on the effect of the pressure of CO 2 on electrocarboxylation processes [27,28].…”

Electrochemical Fixation of Carbon Dioxide

“…Efficient fixation of carbon dioxide in various kinds of organic molecules has been successfully carried out by an electrochemical method with C-C bond formation; alkenes [5] and activated alkenes including styrenes [5][6][7][8][9][10][11][12][13][14][15], allenes [5,16], alkynes [5,[17][18][19], enynes and diynes [5,[20][21][22][23], aromatic [1,3,24], allyl [3,25,26], propargyl [27], benzyl [1,3, and vinyl [3,[51][52][53] halides, aryl [54,55] and vinyl triflates [56][57][58][59][60], aldehydes and ketones [61][62][63][64], imines [65], benzyl esters and carbonates …”