A green, efficient N-alkylation of amines with simple alcohols has been achieved in aqueous solution via an electrochemical version of the so-called “borrowing hydrogen methodology”. Catalyzed by Ru on activated carbon cloth (Ru/ACC), the reaction works well with methanol, and with primary and secondary alcohols. Alkylation can be accomplished by either of two different electrocatalytic processes: (1) in an undivided cell, alcohol (present in excess) is oxidized at the Ru/ACC anode; the aldehyde or ketone product condenses with the amine; and the resulting imine is reduced at an ACC cathode, combining with protons released by the oxidation. This process consumes stoichiometric quantities of current. (2) In a membrane-divided cell, the current-activated Ru/ACC cathode effects direct C–H activation of the alcohol; the resulting carbonyl species, either free or still surface-adsorbed, condenses with amine to form imine and is reduced as in (1). These alcohol activation processes can alkylate primary and secondary aliphatic amines, as well as ammonia itself at 25–70 °C and ambient pressure.

中文翻译：

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通过直接和间接借位氢机理将胺与醇进行电活化烷基化

在水溶液中，通过简单的醇可实现胺的绿色高效N-烷基化所谓的“借用氢方法”的电化学形式。在活性炭布（Ru / ACC）上，通过Ru催化，该反应在甲醇，伯醇和仲醇中均能很好地进行。烷基化可以通过两种不同的电催化方法之一完成：（1）在未分隔的电池中，醇（过量存在）在Ru / ACC阳极被氧化；醛或酮产物与胺缩合；并在ACC阴极还原生成的亚胺，并与氧化释放的质子结合。该过程消耗化学计量的电流。（2）在膜分裂的电池中，电流激活的Ru / ACC阴极直接影响乙醇的C–H激活；所得的游离或仍表面吸附的羰基物质与胺缩合形成亚胺，并按（1）所述还原。