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Synfacts 2008(3): 0302-0302  
DOI: 10.1055/s-2008-1042736
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Direct Aminoalkylation via Nickel-Catalyzed Negishi Cross-Coupling Reactions

Contributor(s): Paul Knochel, Tobias Thaler
L. Melzig, A. Gavryushin, P. Knochel*
Ludwig-Maximilians-Universität München, Germany
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Publication History

Publication Date:
21 February 2008 (online)

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Significance

A new general method for the one-pot introduction of aminoalkyl groups via Negishi-type cross-coupling is reported. It was applied to the cross-coupling with both aryl and hetaryl halides and triflates furnishing the respective products with good to excellent yields. It is noteworthy that cross-coupling of tropanyl zinc reagents proceeds with 100% exo-selectivity. This is due to the stereospecific formation of the corresponding Grignard reagent.