Ruthenium-catalyzed selective α-deuteration of aliphatic nitriles using D2O.

doi:10.1039/c8cc03971b

Paper

Ruthenium-catalyzed selective α-deuteration of aliphatic nitriles using D2O.

Published Aug 2, 2018 · V. Krishnakumar, C. Gunanathan

Chemical communications

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Abstract

Selective catalytic α-deuteration of aliphatic nitriles using deuterium oxide as a deuterium source is reported. A PNP-ruthenium pincer complex catalyzed the α-deuteration of aliphatic nitriles including acetonitrile. Efficient deuteration occurred with a low catalyst load (0.2 to 0.5 mol%) and under mild conditions. A [2+2] cycloadduct formation from nitrile functionality and a deprotonated catalytic intermediate, followed by an imine-enamine tautomerization and a H/D exchange between the enamine intermediate and deuterium oxide leading to the selective deuteration at the α-position of the nitrile, is proposed as a plausible reaction mechanism.

Study Snapshot

Ruthenium-catalyzed selective -deuteration of aliphatic nitriles using deuterium oxide enables efficient deuteration with low catalyst load and mild conditions, potentially benefiting pharmaceutical and biotechnology industries.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Ruthenium-catalyzed selective α-deuteration of aliphatic nitriles using D2O.

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The ruthenium(II)-catalyzed -alkylation of arylmethyl nitriles using alcohols is a facile, atom-economical transformation that produces water as the only byproduct, with diverse primary alcohols being effective reagents.

Citations

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