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In this study, we describe a practical and facile synthesis of deuterium-labeled indoles via acid-catalyzed hydrogen-deuterium exchange. 3-Substituted indoles were efficiently deuterated through treatment with 20 wt % D 2 SO 4 in CD 3 OD at 60-90 °C. A deuterium incorporation reaction of 3-unsubstituted indoles was accomplished through treatment with CD 3 CO 2 D at 150 °C. The in situ preparation of a 20 wt % D 2 SO 4 /CH 3 OD/D 2 O solution enabled a large-scale and low-cost synthesis of auxins, indole-3-acetic acid-d5 and indole-3-butyric acid-d5.

Deuteration of Indole Compounds: Synthesis of Deuterated Auxins, Indole-3-acetic Acid-d5 and Indole-3-butyric Acid-d5