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Synfacts 2013; 9(1): 0107
DOI: 10.1055/s-0032-1317911
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

Nanoporous Gold Catalyst for the Selective Semihydrogenation of Alkynes

Contributor(s):
Yasuhiro Uozumi
,
Yoichi M. A. Yamada
,
Takuma Sato
Yan M, Jin T, * Ishikawa Y, Minato T, Fujita T, Chen L.-Y, Bao M, Asao N, Chen M.-W, Yamamoto Y. Tohoku University, Sendai, Japan and Dalian University of Technology, P. R of China
Nanoporous Gold Catalyst for Highly Selective Semihydrogenation of Alkynes: Remarkable Effect of Amine Additives.

J. Am. Chem. Soc. 2012;
134: 17536-17542
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Publication History

Publication Date:
17 December 2012 (online)

 
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Key words

nanoporous gold - semihydrogenation - alkynes - amines

Significance

A nanoporous gold catalyst (AuNPore), which was prepared by dealloying a homogeneous Au30Ag70 alloy in nitric acid (70 wt%), catalyzed the semihydrogenation of alkynes with organosilanes and water as the hydrogen source to afford the corresponding alkenes. The reaction of phenylacetylene with PhMe2SiH and water in DMF proceeded in the presence of 2 mol% of AuNPore to give styrene as the sole ­product (method A: 35 °C, 3 h, 96% yield). 1-Dodecyne underwent the semihydrogenation efficiently in acetonitrile with 50 mol% of pyridine (method B: 80 °C, 8 h, 98% yield).


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Comment

The catalytic ability of various catalysts was examined for the semihydrogenation of ­phenylacetylene: AuNPore (96%), AuCl (18%), Au30Ag70 alloy (0%), PdNPore (54%), and Pd/C (20%). The authors proposed the reaction pathway including the generation of the H– on the AuNPore surface ([AuNPore-H]–) and pyridinium cation ([HPy]+) which subsequently react with the alkynes to form the corresponding Z-alkenes.


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