2013 Fiscal Year Final Research Report

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

Research Project

Project/Area Number	23655030
Research Category	Grant-in-Aid for Challenging Exploratory Research
Allocation Type	Multi-year Fund
Research Field	Organic chemistry
Research Institution	The University of Tokyo
Principal Investigator	KANO Naokazu 東京大学, 理学(系)研究科(研究院), 准教授 (00302810)
Project Period (FY)	2011 – 2012
Keywords	リン / 同位体標識 / 重水
Research Abstract	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.