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

M. Haniti S. A. Hamid, C. Liana Allen, Gareth W. Lamb, Aoife C. Maxwell, Hannah C. Maytum, Andrew J. A. Watson and Jonathan M. J. Williams*

*Department of Chemistry, University of Bath, Claverton Down, Bath, BA2 7AY, United Kingdom, Email: j.m.j.williamsbath.ac.uk

M. H. S. A. Hamid, C. L. Allen, G. W. Lamb, A. C. Maxwell, H. C. Maytum, A. J. A. Watson, J. M. J. Williams, J. Am. Chem. Soc., 2009, 131, 1766-1774.

DOI: 10.1021/ja807323a (free Supporting Information)


Abstract

Using 0.5 mol % [Ru(p-cymene)Cl2]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. N-Heterocyclization reactions of primary amines have been achieved, as well as alkylation reactions of primary sulfonamides.


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Borrowing Hydrogen Methodology for Amine Synthesis under Solvent-Free Microwave Conditions

A. J. A. Watson, A. C. Maxwell, J. M. J. Williams, J. Org. Chem., 2011, 76, 2328-2331.


Key Words

Amines, Sulfonamides, Pyrrolidines


ID: J48-Y2009-0430