Reductive Deuteration of Nitriles: The Synthesis of α,α-Dideuterio Amines by Sodium-Mediated Electron Transfer Reactions

Yuxuan Ding; Shihui Luo; Adila Adijiang; Hongye Zhao; Jie An

doi:10.1021/acs.joc.8b01730

Reductive Deuteration of Nitriles: The Synthesis of α,α-Dideuterio Amines by Sodium-Mediated Electron Transfer Reactions

J Org Chem. 2018 Oct 5;83(19):12269-12274. doi: 10.1021/acs.joc.8b01730. Epub 2018 Aug 27.

Authors

Yuxuan Ding¹, Shihui Luo¹, Adila Adijiang¹, Hongye Zhao¹, Jie An¹

Affiliation

¹ College of Science , China Agricultural University , No. 2 Yuanmingyuan West Road , Beijing 100193 , China.

PMID: 30091922
DOI: 10.1021/acs.joc.8b01730

Abstract

The first general reductive deuteration of nitriles under single-electron transfer conditions has been developed for the synthesis of α,α-dideuterio amines. This practical and cost-efficient protocol requires only bench stable and commercially available sodium dispersions and EtOD- d₁ and allows for the reductive deuteration of a variety of nitriles in excellent yields and deuterium incorporations.

Publication types

Research Support, Non-U.S. Gov't