Ruthenium-catalyzed selective α-deuteration of aliphatic nitriles using D2 O

Chemical Communications : Chem Comm
Varadhan Krishnakumar, Chidambaram Gunanathan

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.

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Citations

Mar 30, 2019·Chemical Communications : Chem Comm·Jugal KishoreChidambaram Gunanathan
Feb 12, 2020·Organic Letters·Deepak Ranjan PradhanChidambaram Gunanathan
Feb 23, 2019·Journal of the American Chemical Society·Subramanian Thiyagarajan, Chidambaram Gunanathan
Oct 2, 2020·Organic Letters·Subramanian ThiyagarajanChidambaram Gunanathan
Dec 4, 2021·Mass Spectrometry Reviews·Annelaure DamontJean-Claude Tabet

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Methods Mentioned

BETA
NMR

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