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Synfacts 2024; 20(02): 0145
DOI: 10.1055/s-0043-1772958
DOI: 10.1055/s-0043-1772958
Metals in Synthesis
Nickel-Catalyzed Hydrocyanation of Alkynes Using a Malononitrile as Transnitrilation Reagent
Palermo AF,
Chiu BS. Y,
Patel P,
Rousseaux SA. L.
*
University of Toronto, Canada
Nickel-Catalyzed Reductive Alkyne Hydrocyanation Enabled by Malononitrile and a Formaldehyde Additive.
J. Am. Chem. Soc. 2023;
145: 24981-24989
DOI: 10.1021/jacs.3c10165
Nickel-Catalyzed Reductive Alkyne Hydrocyanation Enabled by Malononitrile and a Formaldehyde Additive.
J. Am. Chem. Soc. 2023;
145: 24981-24989
DOI: 10.1021/jacs.3c10165
Significance
Rousseaux and co-workers disclosed a nickel-catalyzed alkyne hydrocyanation making use of glycolonitrile as active cyanating agent, which is formed in situ by reductive coupling of 2-methyl-2-phenylmalononitrile (MPMN) and formaldehyde.
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Comment
The proposed mechanism is supported by mechanistic studies such as deuterium labeling and anion trapping experiments, ruling out the generation of a nickel-hydride intermediate.
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Publikationsverlauf
Artikel online veröffentlicht:
16. Januar 2024
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