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Reductive cyanation of organic chlorides using CO2 and NH3 via Triphos–Ni(I) species
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Reductive cyanation of organic chlorides using CO2 and NH3 via Triphos–Ni(I) species
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Journal Article
Reductive cyanation of organic chlorides using CO2 and NH3 via Triphos–Ni(I) species
2020
Overview
Cyano-containing compounds constitute important pharmaceuticals, agrochemicals and organic materials. Traditional cyanation methods often rely on the use of toxic metal cyanides which have serious disposal, storage and transportation issues. Therefore, there is an increasing need to develop general and efficient catalytic methods for cyanide-free production of nitriles. Here we report the reductive cyanation of organic chlorides using CO
2
/NH
3
as the electrophilic CN source. The use of tridentate phosphine ligand Triphos allows for the nickel-catalyzed cyanation of a broad array of aryl and aliphatic chlorides to produce the desired nitrile products in good yields, and with excellent functional group tolerance. Cheap and bench-stable urea was also shown as suitable CN source, suggesting promising application potential. Mechanistic studies imply that Triphos-Ni(I) species are responsible for the reductive C-C coupling approach involving isocyanate intermediates. This method expands the application potential of reductive cyanation in the synthesis of functionalized nitrile compounds under cyanide-free conditions, which is valuable for safe synthesis of (isotope-labeled) drugs.
Nitriles are key intermediates in production of pharmaceuticals, agrochemicals and organic materials. Here, the authors report a nickel-catalyzed reductive cyanation of organic chlorides with CO
2
/NH
3
and urea as cyanation reagents to afford a broad range of organic nitriles.
