Stereospecific Cross-Coupling of Secondary Alkyl Trifluoroborates

doi:10.1055/s-0030-1259233

Synfacts 2011(2): 0195-0195
DOI: 10.1055/s-0030-1259233

Metal-Mediated Synthesis

Stereospecific Cross-Coupling of Secondary Alkyl Trifluoroborates

Rezensent(en):Paul Knochel, Tobias Thaler

D. 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

Abstract

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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.

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