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Synfacts 2009(5): 0541-0541  
DOI: 10.1055/s-0028-1088182
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

Ruthenium-Catalyzed Alkylation of Amines and Sulfonamides with Alcohols

Rezensent(en):Paul Knochel, Andrei Gavryushin
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*
University of Bath and GlaxoSmithKline, Stevenage, UK
Ruthenium-Catalyzed N-Alkylation of Amines and Sulfonamides Using Borrowing Hydrogen Methodology
J. Am. Chem. Soc.  2009,  131:  1766-1774  
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Publikationsverlauf

Publikationsdatum:
22. April 2009 (online)

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Key words

amines - N-alkylation - ruthenium - sulfonamides

Significance

This work describes a simple, highly versatile and practical method for the alkylation of primary and secondary amines as well as sulfonamides with various alcohols. A broad range of substrates can be used in this reaction that offers mostly excellent yields of products. This method is especially valuable for the modular synthesis of compounds libraries for pharmaceutical and agrochemical screening.

Comment

The reaction proceeds via the formation of an intermediate aldehyde or ketone from the starting alcohol and its subsequent conversion into an imine. Ruthenium plays the role of hydrogen carrier. Some β-alkoxyalcohols give product mixtures. Hindered amines like diisopropylamine do not react.

Review: For a review on the ”borrowing hydrogen" methodology, see: M. H. S. A. Hamid, P. A. Stanford, J. M. J. Williams Adv. Synth. Catal. 2007, 349, 1555-1575.

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