Catalytic hydrogenation of functionalized amides under basic and neutral conditions

A new, base-free high turnover number (TON) catalyst for hydrogenation of simple and functionalized amides is prepared by reacting [Ru(η 3 -C 3 H 5 )(Ph 2 P(CH 2 ) 2 NH 2 ) 2 ]BF 4 and BH 4 − under hydrogen. The hydrogenation proceeds with C–N cleavage to form the corresponding amine and alcohol. Th...

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Bibliographic Details
Published in:Catalysis science & technology 2015-01, Vol.5 (2), p.1181-1186
Main Authors: John, Jeremy M., Loorthuraja, Rasu, Antoniuk, Evan, Bergens, Steven H.
Format: Article
Language:English
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Summary:A new, base-free high turnover number (TON) catalyst for hydrogenation of simple and functionalized amides is prepared by reacting [Ru(η 3 -C 3 H 5 )(Ph 2 P(CH 2 ) 2 NH 2 ) 2 ]BF 4 and BH 4 − under hydrogen. The hydrogenation proceeds with C–N cleavage to form the corresponding amine and alcohol. The base-free and base-promoted hydrogenations tolerate alcohols, amines, aromatic bromides, chlorides and fluorides, ethers, certain olefins, and N-heterocyclic rings. The reaction was used to deprotect the amine groups in certain acetyl amides to form, for example, an N-heterocyclic amine containing an aryl bromide. The base-free system also selectively hydrogenates N -acyloxazolidinones without epimerization at the α-position, and reduced β-lactams to form the corresponding amino alcohols.
ISSN:2044-4753
2044-4761
DOI:10.1039/C4CY01227E