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Synfacts 2009(3): 0307-0307  
DOI: 10.1055/s-0028-1087703
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

Negishi Cross-Coupling of Substrates Bearing Relatively Acidic Protons

Contributor(s): Paul Knochel, Andrei Gavryushin
G. Manolikakes, C. M. Hernandez, M. A. Schade, A. Metzger, P. Knochel*
Ludwig-Maximilians-Universität München, Germany and Universidad de Malaga, Spain
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Publication History

Publication Date:
19 February 2009 (online)

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Significance

Alkyl- or arylzinc halides are believed to be incompatible with the presence of acidic protons like free OH or NH2 groups. However, in many cases the rate of their protonation allows performing the Negishi cross-coupling even in the presence of such acidic groups. The organozinc compounds are readily available directly from the corresponding halides. This method allows a simple one-pot reaction leading to a new C-C bond formation.