C-H deuteration of organic compounds and potential drug candidates
Gaurav Prakash1, Nilanjan Paul1, Gwyndaf A Oliver2
1Department of Chemistry, IIT Bombay, Powai, Mumbai-400076, India. dmaiti@chem.iitb.ac.in.
Abstract:
C-H deuteration has been intricately developed to satisfy the urgent need for site-selectively deuterated organic frameworks. Deuteration has been primarily used to study kinetic isotope effects of reactions but recently its significance in pharmaceutical chemistry has been discovered. Deuterium labelled compounds have stolen the limelight since the inception of the first FDA-approved deuterated drug, for the treatment of chorea-associated Huntington's disease, and their pharmacological importance was realised by chemists, although surprisingly very late. Various approaches were developed to carry out site-selective deuteration. However, the most common and efficient method is hydrogen isotope exchange (HIE). This review summarises deuteration methods of various organic motifs containing C(sp2)-H and C(sp3)-H bonds utilizing C-H bond functionalisation as a key step along with a variety of catalysts, and exemplifies their biological relevance.
Related Concept Videos
¹H NMR of Labile Protons: Deuterium (²H) Substitution
¹³C NMR: Distortionless Enhancement by Polarization Transfer (DEPT)
Diazonium Group Substitution: –OH and –H
Aldehydes and Ketones with HCN: Cyanohydrin Formation Overview
meta-Directing Deactivators: –NO2, –CN, –CHO, –⁠CO2R, –COR, –CO2H
Nucleophilic Aromatic Substitution: Elimination–Addition


