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Synfacts 2020; 16(08): 0947
DOI: 10.1055/s-0040-1706878
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

α,β-Desaturation of Ketones Catalyzed by Palladium(II) on Gold Nanoparticles Supported on Ceria

Contributor(s):
Yasuhiro Uozumi
,
Ryoko Niimi
Takei D, Yatabe T, Jin X, Yabe T, Mizuno N, Yamaguchi K. * The University of Tokyo, Japan
CeO2‑Supported Pd(II)-on-Au Nanoparticle Catalyst for Aerobic Selective α,β-Desaturation of Carbonyl Compounds Applicable to Cyclohexanones.

ACS Catal. 2020;
10: 5057-5063
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Further Information

Publication History

Publication Date:
21 July 2020 (online)

 
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Key words

palladium catalysis - gold catalysis - desaturation cyclohexanones - cyclohexenones - dioxygen

Significance

Palladium(II) on gold nanoparticles supported on CeO2 (Pd/Au/CeO2) was prepared according to equation 1. Pd/Au/CeO2 catalyzed the desaturation of ketones 1 under open-air conditions to give the corresponding α,β-unsaturated ­ketones 2 in up to >99% yield (eq. 2).


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Comment

Pd/Au/CeO2 was characterized by XPS, XANES, XRD, HAADF-STEM, STEM-EDS and ICP-AES analyses. In the desaturation of cyclohexanone (1a) to cyclohex-2-en-1-one (2a), the catalyst showed a high turnover frequency (122 h–1 based on Pd). This catalysis offers a viable alternative to the ­Saegusa–Ito oxidation.


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