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Synfacts 2013; 9(3): 0337
DOI: 10.1055/s-0032-1318224
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

Hydrogenolysis of Aryl or Benzyl Ethers Using Nickel Nanoparticles

Contributor(s):
Yasuhiro Uozumi
,
Hiroaki Tsuji
Sergeev AG, Webb JD, Hartwig JF * University of California, Berkeley, USA
A Heterogeneous Nickel Catalyst for the Hydrogenolysis of Aryl Ethers without Arene Hydrogenation.

J. Am. Chem. Soc. 2012;
134: 20226-20229
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Further Information

Publication History

Publication Date:
15 February 2013 (online)

 
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Key words

nickel nanoparticles - hydrogenolysis - aryl ethers - benzyl ethers

Significance

Nickel nanoparticles, generated in situ from Ni(CH2TMS)2(TMEDA) and t-BuONa, catalyzed the hydrogenolysis of aryl ethers 1 under H2 in m-xylene to give the corresponding products 2–5 (15 examples). The hydrogenolysis of benzyl ethers 6 also proceeded in the presence of the nickel nanoparticles under H2 atmosphere to afford the corresponding toluenes 7 and phenols 8 (4 examples).


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Comment

The nickel nanoparticles were characterized by TEM, STEM, and EDS analyses. EDS analysis showed that the catalyst contained both nickel and sodium. From this result, the authors propose that t-BuONa stabilizes the nickel nanoparticles.


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