Pd/C‐catalyzed one‐pot Suzuki‐Miyaura cross‐coupling/hydrogenation of pyridine derivatives

Using bromopyridines and methoxyphenyl boronic acid as starting materials, consecutive Suzuki‐Miyaura cross‐coupling and hydrogenation reactions were undertaken using a heterogeneous Pd/C catalyst in one‐pot manner under mild conditions (balloon‐pressure at room temperature for hydrogenation) with e...

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Bibliographic Details
Published in:Journal of heterocyclic chemistry 2021-10, Vol.58 (10), p.2039-2044
Main Authors: Pitna, Dinda B., Tanaka, Nao, Usuki, Toyonobu
Format: Article
Language:English
Subjects:
Catalysts
Cross coupling
Hydrogenation
Leaching
Pyridines
Room temperature
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Summary:Using bromopyridines and methoxyphenyl boronic acid as starting materials, consecutive Suzuki‐Miyaura cross‐coupling and hydrogenation reactions were undertaken using a heterogeneous Pd/C catalyst in one‐pot manner under mild conditions (balloon‐pressure at room temperature for hydrogenation) with excellent yield. To counter Pd leaching as well as catalyst poisoning, addition of an appropriate amount of H2O was crucial to achieving successful AcOH‐promoted hydrogenation, which ensured a selective reduction of the pyridine rings to the corresponding piperidines.
ISSN:0022-152X
1943-5193
DOI:10.1002/jhet.4341