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

Shibin Zhao | Zendy; Tobias Gensch | Zendy; Benjamin Murray | Zendy; Zachary L. Niemeyer | Zendy; Matthew S. Sigman | Zendy; Mark R. Biscoe | Zendy

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

Author(s) -

Shibin Zhao,

Tobias Gensch,

Benjamin Murray,

Zachary L. Niemeyer,

Matthew S. Sigman,

Mark R. Biscoe

Publication year - 2018

Publication title -

science

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 12.556

H-Index - 1186

eISSN - 1095-9203

pISSN - 0036-8075

DOI - 10.1126/science.aat2299

Subject(s) - nucleophile , chemistry , stereospecificity , ligand (biochemistry) , transmetalation , coupling reaction , stereochemistry , phosphine , catalysis , combinatorial chemistry , organic chemistry , receptor , biochemistry

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. Zhaoet 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

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