Umpolung of a Hydrogen Atom of Water by Using a Hexacoordinated Phosphate and Its Application to Deuteride Reduction Reactions of Carbonyl Compounds

被引：18

作者：

Miyake, Hideaki ^{[1
]}

Kano, Naokazu ^{[1
]}

Kawashima, Takayuki ^{[1
]}

机构：

[1] Univ Tokyo, Grad Sch Sci, Dept Chem, Bunkyo Ku, Tokyo 1130033, Japan

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2009年 / 131卷 / 46期

基金：

日本学术振兴会;

关键词：

PHOSPHORANE; REACTIVITY; EXCHANGE; BOND;

D O I：

10.1021/ja906875d

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The polarity of a chemical bond is an important factor that determines the reactivity because a reaction of a positively charged atom with a negatively charged atom easily occurs. We report here a method for reversing the polarity of a hydrogen atom of water, which meant conversion of a protic hydrogen (H(delta+)) to a hydridic hydrogen (H(delta-)), by using a hexacoordinated phosphorus species. The method enables a reductive deuteration of carbonyl compounds utilizing inexpensive and easily usable D2O under mild conditions. The umpolung of a hydrogen atom was achieved by utilizing tautomerization of phosphorus compounds. Classical metal hydrides never have this function, and these results demonstrated the potential utility of nonmetallic compounds for umpolung of a hydrogen atom.

引用

页码：16622 / +

页数：4

共 44 条

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