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Synfacts 2022; 18(10): 1121
DOI: 10.1055/s-0041-1738695
Polymer-Supported Synthesis

Hydroamination of Arylacetylenes by Gold Nanoclusters Immobilized on Carbon

Contributor(s):
Yasuhiro Uozumi
,
Teruki Takahashi
Shen H, Wu Q, Malola S, Han Y.-Z, Xu Z, Qin R, Tang X, Chen Y.-B, Teo BK, Häkkinen H, *, Zheng N. * University of Jyväskylä, Finland; Xiamen University and Innovation Laboratory for Sciences and Technologies of Energy Materials of Fujian Province (IKKEM), Xiamen, P. R. of China
N‑Heterocyclic Carbene-Stabilized Gold Nanoclusters with Organometallic Motifs for Promoting Catalysis.

J. Am. Chem. Soc. 2022;
144: 10844-10853
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Key words

gold catalysis - N-heterocyclic carbenes - hydroamination - phenylacetylenes - anilines

Significance

An N-heterocyclic-carbene-stabilized gold nanocluster [Au16(NHC-1)5(PA)3Br2]3+ (Au16 cluster) immobilized on carbon (Au16/XC-72) was prepared according to Equation 1. Au16/XC-72 catalyzed the hydroamination of arylacetylenes with anilines to give the corresponding ketimines in up to >99% NMR yield (eq. 2).


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Comment

The Au16 cluster was characterized by means of XRD, 1H NMR, 13C NMR, HRESI-MS, UV/Vis, DPV, XANES, EXAFS, and IR analyses. Au16/XC-72 had similar XANES, EXAFS, and IR profiles to a Au16 cluster. The reaction of phenylacet­ylene with aniline catalyzed by 0.002 mol% of Au16/XC-72 proceeded with a high turnover number of 50,000.


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Publication History

Article published online:
20 September 2022

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