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Issue 3, 2012
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General palladium-catalyzed aerobic dehydrogenation to generate double bonds

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Abstract

We describe a general dehydrogenation procedure to form α,β-unsaturated aldehydes, ketones, esters and azobenzenes under very mild conditions, requiring catalytic commercial Pd(OAc)2, a catalytic weak inorganic base and air as the sole oxidant. In the presence of a diazafluorenone ligand, this process converts aliphatic aldehydes to α,β-unsaturated aldehydes in an open-flask fashion at ambient pressure and temperature. A broad spectrum of substrates, including aldehydes, ketones, esters, alcohols and hydrazines, were conveniently dehydrogenated under a relatively uniformed protocol. A mechanism involving β-elimination-driven enolization equilibrium shift was proposed.

Graphical abstract: General palladium-catalyzed aerobic dehydrogenation to generate double bonds

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Publication details

The article was received on 11 Sep 2011, accepted on 07 Nov 2011 and first published on 07 Nov 2011


Article type: Edge Article
DOI: 10.1039/C1SC00661D
Citation: Chem. Sci., 2012,3, 883-886
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    General palladium-catalyzed aerobic dehydrogenation to generate double bonds

    W. Gao, Z. He, Y. Qian, J. Zhao and Y. Huang, Chem. Sci., 2012, 3, 883
    DOI: 10.1039/C1SC00661D

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