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, Liming Zhang

Research output: Contribution to journalArticlepeer-review

84 Scopus citations

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.

Original languageEnglish (US)
Article number3470
Pages (from-to)3470
Number of pages1
JournalNature communications
Volume5
DOIs
StatePublished - 2014

Bibliographical note

Funding Information:
We appreciate the financial support of NIH (NIGMS (R01 GM084254), NSF (CHE-1301343) and the Natural Science Foundation of China (Grant number 21172248, 21121062).

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