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A general ligand design for gold catalysis allowing ligand-directed anti-nucleophilic attack of alkynes

Author

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  • Yanzhao Wang

    (University of California)

  • Zhixun Wang

    (University of California)

  • Yuxue Li

    (State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry)

  • Gongde Wu

    (University of California)

  • Zheng Cao

    (University of California)

  • Liming Zhang

    (University of California)

Abstract

Most homogenous gold catalyses demand ≥0.5 mol% catalyst loading. Owing to the high cost of gold, these reactions are unlikely to be applicable in medium- or large-scale applications. Here we disclose a novel ligand design based on the privileged (1,1′-biphenyl)-2-ylphosphine framework that offers a potentially general approach to dramatically lowering catalyst loading. In this design, an amide group at the 3′-position of the ligand framework directs and promotes nucleophilic attack at the ligand gold complex-activated alkyne, which is unprecedented in homogenous gold catalysis considering the spatial challenge of using ligand to reach anti-approaching nucleophile in a linear P-Au-alkyne centroid structure. With such a ligand, the gold(I) complex becomes highly efficient in catalysing acid addition to alkynes, with a turnover number up to 99,000. Density functional theory calculations support the role of the amide moiety in directing the attack of carboxylic acid via hydrogen bonding.

Suggested Citation

  • Yanzhao Wang & Zhixun Wang & Yuxue Li & Gongde Wu & Zheng Cao & Liming Zhang, 2014. "A general ligand design for gold catalysis allowing ligand-directed anti-nucleophilic attack of alkynes," Nature Communications, Nature, vol. 5(1), pages 1-8, May.
    • Handle: RePEc:nat:natcom:v:5:y:2014:i:1:d:10.1038_ncomms4470
    DOI: 10.1038/ncomms4470
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