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


Reference:

Hamid, M. H. S. A., Allen, C. L., Lamb, G. W., Maxwell, A. C., Maytum, H. C., Watson, A. J. A. and 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), pp. 1766-1774.

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http://dx.doi.org/10.1021/ja807323a

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.

Details

Item Type Articles
CreatorsHamid, M. H. S. A., Allen, C. L., Lamb, G. W., Maxwell, A. C., Maytum, H. C., Watson, A. J. A. and Williams, J. M. J.
DOI10.1021/ja807323a
DepartmentsFaculty of Science > Chemistry
Faculty of Engineering & Design > Chemical Engineering
RefereedYes
StatusPublished
ID Code13997

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