Synthesis 2019; 51(06): 1319-1328
DOI: 10.1055/s-0037-1610405
short review
© Georg Thieme Verlag Stuttgart · New York

40 Years of Hydrogen–Deuterium Exchange Adjacent to Heteroatoms: A Survey

Alessia Michelotti
a  CortecNet, 15-17 Rue des Tilleuls, 78960, Voisins-le-Bretonneux, France   Email: mroche@cortecnet.com
b  Institut Lavoisier de Versailles, UMR 8180 CNRS, Université de Versailles Saint-Quentin-en-Yvelines, 78035, Versailles, France
,
a  CortecNet, 15-17 Rue des Tilleuls, 78960, Voisins-le-Bretonneux, France   Email: mroche@cortecnet.com
› Author Affiliations
A.M. thanks the Research Executive Agency (REA), Marie Sklodowska-Curie Innovative Training Network for a Ph.D. fellowship (EUROPOL project, grant number 642773).
Further Information

Publication History

Received: 31 August 2018

Accepted after revision: 30 October 2018

Publication Date:
09 January 2019 (eFirst)

Abstract

Deuteration of bioactive molecules is gaining more and more attention, especially after the approval of the first deuterated drug (Austedo™) by the US Food and Drug Administration (FDA). Not only is deuteration important for drug development, the amount of deuterium in a molecule is critical for the production of standards in mass spectrometry and the selectivity of the deuteration is mandatory for NMR applications. Very frequently, the molecules involved in these applications contain several heteroatoms. It has been demonstrated that oxygen-, nitrogen-, and more recently, sulfur-containing molecules can be easily deuterated at the α position leading to high deuterium incorporation. In this review we will focus our attention on the historical background and the recent progress made on heteroatom-directed deuteration, with particular attention on the catalysts and the mechanisms that drive such transformations.

1 Introduction

2 Oxygen-Directed Deuteration

3 Nitrogen-Directed Deuteration

4 Sulfur-Directed Deuteration

5 Conclusion

 
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