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Synfacts 2015; 11(11): 1215
DOI: 10.1055/s-0035-1560664
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

Aerobic Cross-Dehydrogenative Coupling with Nanoporous Gold

Contributor(s):
Yasuhiro Uozumi
,
Takao Osako
Ho HE, Ishikawa Y, Asao N, Yamamoto Y, Jin T * Tohoku University, Sendai, Japan and Dalian University of Technology, P. R. of China
Highly Efficient Heterogeneous Aerobic Cross-Dehydrogenative Coupling via C–H Functionalization of Tertiary Amines Using a Nanoporous Gold Skeleton Catalyst.

Chem. Commun. 2015;
51: 12764-12767
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Publication History

Publication Date:
19 October 2015 (online)

 
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Key words

nanoporous catalysts - gold - cross-dehydrogenative coupling - tertiary amines - aerobic conditions

Significance

Zero-valent nanoporous gold (AuNPore) catalyzed the cross-dehydrogenative coupling of tertiary amines with carbon nucleophiles in the presence of oxygen or tert-butyl hydroperoxide to give the corresponding C–C coupling products in ≤98% isolated yield (eq. 1; 24 examples). After the reaction, the catalyst was recovered by filtration and reused nine times without loss of catalytic activity.


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Comment

The authors previously reported the preparation of AuNPore (J. Am. Chem. Soc. 2012, 134, 17536). The catalytic activity of AuNPore for the cross-dehydrogenative coupling was superior to that of other nanoporous metal catalysts, such as nanoporous silver, copper, palladium, or platinum. An SEM study revealed that the morphology, pore size, and nanoporosity of AuNPore were unchanged after the catalytic reaction. ICP-MS analysis of the reaction solution showed no leaching of gold from the catalyst.


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