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Reductive N-alkylation of primary and secondary amines using carboxylic acids and borazane under mild conditions

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Abstract

An expedient strategy of reductive N-alkylation of amines with readily available carboxylic acids as alkylating reagents has been developed. Commercially available and hydrogen rich ammonia borane (H3B·NH3) was employed as a practical hydrogen source. Mono- and dialkylated products of primary amines could be selectively obtained by varying the reaction conditions. Complementary to known reductive aminations, this strategy showed excellent functional group compatibility, and a broad range of secondary and tertiary amines, including drug molecules, were obtained smoothly.

Graphical abstract: Reductive N-alkylation of primary and secondary amines using carboxylic acids and borazane under mild conditions

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Publication details

The article was received on 31 Aug 2018, accepted on 28 Sep 2018 and first published on 28 Sep 2018


Article type: Research Article
DOI: 10.1039/C8QO00942B
Citation: Org. Chem. Front., 2018, Advance Article
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    Reductive N-alkylation of primary and secondary amines using carboxylic acids and borazane under mild conditions

    Y. Wei, Q. Xuan, Y. Zhou and Q. Song, Org. Chem. Front., 2018, Advance Article , DOI: 10.1039/C8QO00942B

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