Visible light driven deuteration of formyl C-H and hydridic C(sp3)-H bonds in feedstock chemicals and pharmaceutical molecules.

Chemical Science
Yulong KuangJie Wu

Abstract

Deuterium labelled compounds are of significant importance in chemical mechanism investigations, mass spectrometric studies, diagnoses of drug metabolisms, and pharmaceutical discovery. Herein, we report an efficient hydrogen deuterium exchange reaction using deuterium oxide (D2O) as the deuterium source, enabled by merging a tetra-n-butylammonium decatungstate (TBADT) hydrogen atom transfer photocatalyst and a thiol catalyst under light irradiation at 390 nm. This deuteration protocol is effective with formyl C-H bonds and a wide range of hydridic C(sp3)-H bonds (e.g. α-oxy, α-thioxy, α-amino, benzylic, and unactivated tertiary C(sp3)-H bonds). It has been successfully applied to the high incorporation of deuterium in 38 feedstock chemicals, 15 pharmaceutical compounds, and 6 drug precursors. Sequential deuteration between formyl C-H bonds of aldehydes and other activated hydridic C(sp3)-H bonds can be achieved in a selective manner.

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Citations

Oct 2, 2020·Angewandte Chemie·Matthias SchmalzbauerBurkhard König
Nov 24, 2020·Journal of Labelled Compounds & Radiopharmaceuticals·Volker Derdau
Jun 25, 2021·Chemical Science·Nian LiChengjian Zhu
May 13, 2021·Organic & Biomolecular Chemistry·Masahiro UedaHiroshi Matsubara
Jul 15, 2021·Organic Letters·Tobias E SchirmerBurkhard König
Aug 7, 2021·Chemical Reviews·Luca CapaldoMaurizio Fagnoni
Oct 9, 2021·Chemical Reviews·Kelvin Pak Shing CheungVladimir Gevorgyan

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