Programmable Deuteration of Indoles via Reverse Deuterium Exchange
Liam S. Fitzgerald, Rachael L. McNulty, Andrew Greener, Miriam L. O’Duill
Abstract
Methods for selective deuterium incorporation into drug-like molecules have become extremely valuable due to the commercial, mechanistic, and biological importance of deuterated compounds. Herein, we report a programmable labeling platform that allows access to C2, C3, or C2- and C3-deuterated indoles under mild, user-friendly conditions. The C2-deuterated indoles are accessed using a reverse hydrogen isotope exchange strategy which represents the first non-directed C2-deuteration of indoles.
Topics & Concepts
ChemistryDeuteriumHydrogen–deuterium exchangeCombinatorial chemistryMoleculeIsotopic labelingHydrogenOrganic chemistryNuclear physicsPhysicsChemical Reactions and IsotopesAsymmetric Hydrogenation and CatalysisChemical Synthesis and Analysis