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Iridium-catalyzed Csp3-H activation for mild and selective hydrogen isotope exchange

Kerr, William J. and Mudd, Richard J. and Reid, Marc and Atzrodt, Jens and Derdau, Volker (2018) Iridium-catalyzed Csp3-H activation for mild and selective hydrogen isotope exchange. ACS Catalysis, 8. 10895–10900. ISSN 2155-5435

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    Abstract

    The increasing demand for isotopically labeled compounds has provided appreciable impetus for the development of improved methods for the late stage introduction of isotopes of hydrogen (deuterium or tritium). Moreover, sp3-rich molecules are becoming increasingly common in the exploration of chemical space for drug design. Herein, we report an efficient iridium(I) catalysed C-H activation method for the hydrogen isotope exchange of sp3 C-H bonds. A wide range of substrates have been labeled, including active pharmaceutical ingredients, delivering excellent levels of isotope incorporation and predictable regiocontrol, with low catalyst loadings, in short reaction times, and under mild reaction conditions.