Ruthenium-catalyzed N-alkylation of amines and sulfonamides using borrowing hydrogen methodology

M H S A Hamid, C L Allen, Gareth W Lamb, A C Maxwell, Hannah C Maytum, Andrew J A Watson, Jonathan M J Williams

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Abstract

The alkylation of amines by alcohols has been achieved using 0.5 mol % [Ru(p-cymene)Cl-2](2) with the bidentate phosphines dppf or DPEphos as the catalyst. Primary amines have been converted into secondary amines, and secondary amines into tertiary amines, including the syntheses of Piribedil, Tripelennamine, and Chlorpheniramine. N-Heterocyclization reactions of primary amines are reported, as well as alkylation reactions of primary sulfonamides. Secondary alcohols require more forcing conditions than primary alcohols but are still effective alkylating agents in the presence of this catalyst.
Original languageEnglish
Pages (from-to)1766-1774
Number of pages9
JournalJournal of the American Chemical Society
Volume131
Issue number5
Early online date21 Jan 2009
DOIs
Publication statusPublished - 11 Feb 2009

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    Hamid, M. H. S. A., Allen, C. L., Lamb, G. W., Maxwell, A. C., Maytum, H. C., Watson, A. J. A., & Williams, J. M. J. (2009). Ruthenium-catalyzed N-alkylation of amines and sulfonamides using borrowing hydrogen methodology. Journal of the American Chemical Society, 131(5), 1766-1774. https://doi.org/10.1021/ja807323a