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.

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