Abstract
A method for the selective deuteration of polyfunctional organic molecules using catalytic amounts of [RuCl2(PPh3)3] and D2O as a deuterium source is presented. Through variation of additives like CuI, KOH, and various amounts of zinc powder, orthogonal chemoselectivities in the deuteration process are observed. Mechanistic investigation indicates the presence of different, defined Ru‐complexes under the given specific conditions.
Highlights
The exchange of hydrogen atoms for their isotopes deuterium or tritium is a common method for studies on biosynthesis and metabolism.[1]
The activity of the structurally similar complex [RuHCl(PPh3)3] in the chemoselective reduction of olefins in the presence of carbonyl groups has been described in the literature.[9]
Since the ortho-selective H–D exchange occurs with addition of catalytic amounts of KOD even without zinc, a direct deuteration from D2O can be assumed under these conditions
Summary
The exchange of hydrogen atoms for their isotopes deuterium or tritium is a common method for studies on biosynthesis and metabolism.[1]. The H–D exchange at the acidic a-carbon atom occurs as a KOD-catalyzed background reaction, and the addition of [RuCl2(PPh3)3] 1 was not necessary under these conditions. In the presence of CuI as an additive, no reduction of the carbonyl group and no deuteration at the a-carbon atom was observed.
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