Pyridines can be deuterated at the remote sites by treatment with KOtBu in DMSO-d6, although without discrimination between the meta- and para-position. Herein, base-catalyzed deuterations have been studied, computationally and experimentally, using a series of pyridyl phosphonium salts with a temporary electron-withdrawing group to block the para-position while increasing the acidity in the other positions.
Mechanistic insights into the base-mediated deuteration of pyridyl phosphonium and ammonium salts
Andrea Citarella;
2025-01-01
Abstract
Pyridines can be deuterated at the remote sites by treatment with KOtBu in DMSO-d6, although without discrimination between the meta- and para-position. Herein, base-catalyzed deuterations have been studied, computationally and experimentally, using a series of pyridyl phosphonium salts with a temporary electron-withdrawing group to block the para-position while increasing the acidity in the other positions.
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