Development of a nucleophilic deuteration method by using heavy water without any transition metal

以重水为催化剂，在温和条件下，在无过渡金属存在的条件下，进行了羰基化合物的重水还原反应。合成了含两个P-H键的ATE型六配位磷化合物作为稳定化合物。分离出磷原子周围的两个异构体。两种异构体对重水均表现出H-D交换反应活性，对羰基化合物表现出氢化还原反应活性。一种异构体的反应活性与另一种异构体的反应活性不同。找到了这两个反应一锅反应的反应条件，并用重水对羰基化合物进行了正式还原。因此，我们成功地发展了一种重水亲核还原氢化方法。

Deuteride reduction reactions of carbonyl compounds were developed by using the umpolung of heavy water under mild conditions without the presence of a transition metal. Ate-type hexacoordinated phosphorus compounds bearing two P-H bonds were synthesized as stable compounds. Two isomers around the phosphorus atom were isolated. Both isomers showed H-D exchange reactivity toward heavy water and hydride reduction reactivity toward carbonyl compounds. The reactivities of one isomer differ from those of the other isomer. Reaction conditions for the one-pot reaction of these two reactions were found, and the carbonyl compounds were formally reduced with heavy water. Therefore, a nucleophilic reductive deuteration method by using heavy water were successfully developed.