Synthesis of α-Deuterated Primary Amines via Reductive Deuteration of Oximes Using D2O as a Deuterium Source

Lei Ning, Hengzhao Li, Zemin Lai, Michal Szostak, Xingyue Chen, Yanhong Dong, Shuhui Jin, Jie An

Research output: Contribution to journalArticlepeer-review

1 Scopus citations

Abstract

Selective introduction of the deuterium atom into the α-position of amines is important for the development of all types of novel deuterated drugs and agrochemicals due to the pervasive presence of amines. In this study, we report the first general single-electron-transfer reductive deuteration of both ketoximes and aldoximes using SmI2 as an electron donor and D2O as a deuterium source for the synthesis of α-deuterated primary amines with excellent levels of deuterium incorporations (>95% [D]). This protocol exhibits excellent chemoselectivity and tolerates a variety of functional groups. The potential application of this new method was showcased in the synthesis of deuterated drugs, such as rimantadine-d4, the tebufenpyrad analogue, derivatives of nabumetone and pregnenolone, and a series of building blocks for the rapid and general assembly of deuterated drugs and pesticides.

Original languageEnglish (US)
Pages (from-to)2907-2916
Number of pages10
JournalJournal of Organic Chemistry
Volume86
Issue number3
DOIs
StatePublished - Feb 5 2021

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

Fingerprint

Dive into the research topics of 'Synthesis of α-Deuterated Primary Amines via Reductive Deuteration of Oximes Using D<sub>2</sub>O as a Deuterium Source'. Together they form a unique fingerprint.

Cite this