Site-selective deuteration of N-heterocycles via iridium-catalyzed hydrogen isotope exchange

Kerr, William J. and Lindsay, David M. and Owens, Philippa K. and Reid, Marc and Tuttle, Tell and Campos, Sébastien (2017) Site-selective deuteration of N-heterocycles via iridium-catalyzed hydrogen isotope exchange. ACS Catalysis, 7 (10). 7182–7186. ISSN 2155-5435

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    Abstract

    The application of iridium(I) NHC/phosphine catalysts has delivered highly selective deuteration of indole, azaindole, and pyrrole N-heterocycles, which represent an important and relatively underexplored class of labeling substrates. Common N-protecting groups have been used to selectively direct C–H activation, and can be removed under mild conditions with retention of the deuterium label. The method is exemplified by the labeling of drug molecule Sumatriptan. Complementary DFT studies have been conducted to facilitate the rationalization of the very good selectivity offered by the mild and convenient labeling process.