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Synfacts 2011(2): 0195-0195
DOI: 10.1055/s-0030-1259233
DOI: 10.1055/s-0030-1259233
Metal-Mediated Synthesis
© Georg Thieme Verlag
Stuttgart ˙ New York
Stereospecific Cross-Coupling of Secondary Alkyl Trifluoroborates
Contributor(s):Paul Knochel, Tobias ThalerD. L. Sandrock, L. Jean-Gérard, C.-y. Chen, S. D. Dreher, G. A. Molander*
University of Pennsylvania, Philadelphia and Merck Research Laboratories, Rahway, USA
Stereospecific Cross-Coupling of Secondary Alkyl β-Trifluoroboratoamides
J. Am. Chem. Soc. 2010, 132: 17108-17110
University of Pennsylvania, Philadelphia and Merck Research Laboratories, Rahway, USA
Stereospecific Cross-Coupling of Secondary Alkyl β-Trifluoroboratoamides
J. Am. Chem. Soc. 2010, 132: 17108-17110
Further Information
Publication History
Publication Date:
19 January 2011 (online)
Key words
cross-coupling - C-C coupling - stereospecificity - organotrifluoroborates - palladium
Significance
The cross-coupling of β-trifluoroboratoamides was shown to proceed with high selectivity. Thereby, the carbonyl group of the amide moiety serves as a hemilabile ligand inhibiting the undesired β-H-elimination pathway.
Comment
This remarkable cross-coupling of enantioenriched nonbenzylic secondary alkyl boron compounds with aryl halides was shown to proceed stereospecifically with inversion of configuration. This stereochemical outcome is attributed to an intramolecular coordination of the carbonyl group to the boron.