Ruthenium-Catalyzed N-Alkylation of Amines and Sulfonamides Using Borrowing Hydrogen Methodology

Hamid, M. Haniti S. A. and Allen, C. Liana and Lamb, Gareth W. and Maxwell, Aoife C. and Maytum, Hannah and Watson, Andrew J. A. and Williams, Jonathan M. J. (2009) Ruthenium-Catalyzed N-Alkylation of Amines and Sulfonamides Using Borrowing Hydrogen Methodology. Journal of the American Chemical Society, 131 (5). pp. 1766-1774. ISSN 0002-7863

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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.

Item Type:
Journal Article
Journal or Publication Title:
Journal of the American Chemical Society
Uncontrolled Keywords:
/dk/atira/pure/subjectarea/asjc/1500/1503
Subjects:
ID Code:
84282
Deposited By:
Deposited On:
25 Jan 2017 09:02
Refereed?:
Yes
Published?:
Published
Last Modified:
26 Mar 2020 05:12