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首页> 外文期刊>Chemistry: A European journal >Ruthenium-catalyzed regioselective deuteration of alcohols at the β-carbon position with deuterium oxide
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Ruthenium-catalyzed regioselective deuteration of alcohols at the β-carbon position with deuterium oxide

机译：钌催化氧化的β-碳原子上的醇区域选择性氘化

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摘要

A convenient method for regioselective H/D exchange between D_2O and alcohols at the β-carbon position using the catalytic system [(p-cymene)RuCl_2]/ethanolamine/KOH is described. This method is applicable for deuteration of both primary and secondary alcohols. The H/D exchange reactions proceed through an oxidation/modification/reduction reaction sequence. Alcohols are first temporarily oxidized to carbonyl compounds by the hydrogen transfer catalyst. The carbonyl compounds then undergo deuteration at the carbon adjacent to the carbonyl group by keto-enol tautomerization in the presence of D_2O and a catalytic amount of base. The deuterated carbonyl compounds are then reduced to produce deuterated alcohols. In support of the reaction mechanism, a well-defined bimetallic ruthenium complex was isolated from the reaction of [{(p-cymene)RuCl_2}_2] with ethanolamine. The activity of this complex is similar to that of [{(p-cymene)RuCl_2}_2]/ethanolamine.
机译：描述了一种使用催化体系[（对异丙基）RuCl_2] /乙醇胺/ KOH在D_2O和位于β-碳位置的醇之间进行区域选择性H / D交换的简便方法。该方法适用于伯醇和仲醇的氘化。 H / D交换反应通过氧化/修饰/还原反应顺序进行。首先，通过氢转移催化剂将醇暂时氧化为羰基化合物。然后，在D_2O和催化量的碱存在下，通过酮-烯醇互变异构作用使羰基化合物在与羰基相邻的碳原子上进行氘化。然后将氘代羰基化合物还原以产生氘代醇。为了支持该反应机理，从[{（对-cymene）RuCl_2}} _ 2与乙醇胺的反应中分离出了明确定义的双金属钌配合物。该络合物的活性类似于[{（对-cymene）RuCl_2} _2] /乙醇胺的活性。

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