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

Yanzhao Wang, Zhixun Wang, Yuxue Li (), Gongde Wu, Zheng Cao and Liming Zhang ()
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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

Nature Communications, 2014, vol. 5, issue 1, 1-8

Abstract: 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.

Date: 2014
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DOI: 10.1038/ncomms4470

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