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Synfacts 2013; 9(5): 0535
DOI: 10.1055/s-0033-1338330
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Catalytic Semireduction of Alkynes to Alkenes

Authors

    Contributor(s):

  • Paul Knochel

  • Andreas K. Steib

Whittaker AM, Lalic G * University of Washington, Seattle, USA
Monophasic Catalytic System for the Selective Semireduction of Alkynes.

Org. Lett. 2013;
15: 1112-1115
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Further Information

Publication History

Publication Date:
17 April 2013 (online)

 
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Key words

copper - polymethylhydrosiloxane - alkynes

Significance

A novel copper-catalyzed semireduction of alkynes to alkenes has been disclosed. 0.5 to 2 mol% of a copper catalyst in combination with polymethylhydrosiloxane and isobutyl alcohol efficiently reduced terminal and internal alkynes, even in the presence of nitro and iodo groups.


 

Comment

The authors propose the following mechanism: the silane transfers its hydride to the copper catalyst and a subsequent hydrocupration of the alkyne takes place. Protonation of this alkenyl-copper intermediate by the alcohol forms a copper alkoxide and the desired product.


 

 


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