Enantiodivergent Pd-catalyzed C–C bond formation enabled through ligand parameterization

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Science  09 Nov 2018:
Vol. 362, Issue 6415, pp. 670-674
DOI: 10.1126/science.aat2299

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The staying power of electron-poor ligands

The venerable Suzuki coupling reaction originally used palladium to pair up unsaturated carbon centers. The protocol has been widely extended to chiral saturated alkyl carbons, but control over product stereochemistry is a pressing challenge. Zhao et al. systematically studied how the properties of the phosphine ligands that are coordinated to the catalyst influence the stereochemical outcome. Certain electron-withdrawing phosphines favored retention of the initial configuration in chiral alkyltrifluoroborate reactants. Conversely, bulky electron-rich phosphines lead to inverted configurations in the products.

Science, this issue p. 670