Issue 3, 2012

General palladium-catalyzed aerobic dehydrogenation to generate double bonds

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

Supplementary files

Article information

Article type
Edge Article
Submitted
11 Sep 2011
Accepted
07 Nov 2011
First published
07 Nov 2011

Chem. Sci., 2012,3, 883-886

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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