北海道大学 · 化学工学
Senboku教授の研究室は、電気化学的反応を活用した二酸化炭素の効率的固定を柱としています。特に、アルケンやアルデヒド誘導体、α-アミノスルホン酸誘導体を原料として、炭素–炭素結合形成とCO₂の効果的導入を組み合わせた新規合成法を開発しています。反応は大気圧CO₂下でPt電極とMgアンソードを用いるシンプルな電解セルで実現され、非対称アルキル化やラジカルシクロ化を介した多機能的化合物の合成が可能です。医薬品中間体や非ステロイド性消炎薬（NSAIDs）の新規合成への応用も進んでいます。
Figures are computed from collected data and may differ slightly.
Electrochemical dicarboxylation of phenyl-substituted alkenes in the presence of atmospheric pressure of carbon dioxide with a platinum plate cathode and a magnesium rod anode readily took place efficiently in a DMF solution containing 0.1 M Et4NClO4 to give the corresponding 1,2-dicarboxylic acids in high yields.
In the past three decades, we have focused on the fixation of carbon dioxide by electrochemical method with a carbon-carbon bond forming reaction to yield carboxylic acid, so-called electrochemical carboxylation. Vinyl bromides and triflates, difluoroethylbenzenes, polyfluoroarenes, benzal diacetates, phenyl-substituted alkenes and enamides, and α-aminosulfones were found to be effective as substrates for electrochemical carboxylation. Phenylacetic acids and phenylpropanoic acids including non-s
Facile synthesis of 2,3-dihydrobenzofuran-3-ylacetic acids and related analogues was successfully carried out by a novel electrochemical aryl radical generation and its 5-exo cyclization followed by a carboxylation sequence of 2-allyloxybromobenzenes by using methyl 4-tert-butylbenzoate as an electron-transfer mediator.
Electrochemical reduction of N-Boc-α-aminosulfones in DMF using an undivided cell equipped with a Pt plate cathode and an Mg rod anode under atmospheric pressure of bubbling carbon dioxide through the solution under constant current conditions resulted in a reductive C–S bond cleavage with elimination of benzenesulfinate ion generating the corresponding anion species followed by fixation of carbon dioxide to give the corresponding N-Boc-α-amino acids in moderate to good yields.
Electrochemical carboxylation of α,α-difluorotoluene derivatives resulted in an efficient fixation of carbon dioxide to give the corresponding α-fluorophenylacetic acids in good yields, and this reaction was successfully applied to the synthesis of α-fluorinated nonsteroidal anti-inflammatory drugs (NSAIDs).
Abstract Efficient synthesis of mandel acetate, 2‐acetoxy‐2‐phenylacetic acid, from benzaldehyde was successfully performed in two steps using electrochemical carboxylation of benzal diacetate as a key step. When benzal diacetate, readily prepared from benzaldehyde and acetic anhydride in one step, in DMF containing 0.1 M Bu 4 NBF 4 was electrolyzed in the presence of carbon dioxide using an undivided cell equipped with a platinum plate cathode and a magnesium rod anode under constant current co
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