Fast and Efficient Nickel(II)‐catalysed Transfer Hydrogenation of Quinolines with Ammonia Borane

Fast and Efficient Nickel(II)‐catalysed Transfer Hydrogenation of Quinolines with Ammonia Borane

Herein we report the first Ni(II)‐catalysed transfer hydrogenation of quinolines using ammonia borane (AB) as hydrogen (H2) source. An in situ generated Ni(II)‐bis(pyrazolyl)pyridine pre‐catalyst could hydrogenate quinoline and its derivatives in excellent yields of up to 90% at 25 °C in 30 minutes....

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Veröffentlicht in:Advanced synthesis & catalysis 2020-12, Vol.362 (24), p.5788-5793
Hauptverfasser: Vermaak, Vincent, Vosloo, Hermanus C. M., Swarts, Andrew J.
Format: Artikel
Sprache:eng
Schlagworte:
Ammonia
Ammonia Borane
Boranes
Chemistry
Chemistry, Applied
Chemistry, Organic
Hydrogen storage
Hydrogenation
Nickel
Nickel(II)
Organic compounds
Physical Sciences
Quinoline
Quinolines
Science & Technology
Transfer hydrogenation
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Zusammenfassung:Herein we report the first Ni(II)‐catalysed transfer hydrogenation of quinolines using ammonia borane (AB) as hydrogen (H2) source. An in situ generated Ni(II)‐bis(pyrazolyl)pyridine pre‐catalyst could hydrogenate quinoline and its derivatives in excellent yields of up to 90% at 25 °C in 30 minutes. Spectroscopic studies revealed that a Ni(II)‐hydride is responsible for the transfer hydrogenation of quinoline to 1,2,3,4‐tetrahydroquinoline via a 1,4‐dihydroquinoline intermediate.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.202001147