I have a soft-spot for catalyst chemistry. My Science magazine from 8 July 2011 fell behind my desk and I just read through it and found something very exciting. The abstract is below, but also here.
"Palladium-Catalyzed Aerobic Dehydrogenation of Substituted Cyclohexanones to Phenols"
Aromatic molecules are key constituents of many pharmaceuticals, electronic materials, and commodity plastics. The utility of these molecules directly reflects the identity and pattern of substituents on the aromatic ring. Here, we report a palladium(II) catalyst system, incorporating an unconventional ortho-dimethylaminopyridine ligand, for the conversion of substituted cyclohexanones to the corresponding phenols. The reaction proceeds via successive dehydrogenation of two saturated carbon-carbon bonds of the six-membered ring and uses molecular oxygen as the hydrogen acceptor. This reactivity demonstrates a versatile and efficient strategy for the synthesis of substituted aromatic molecules with fundamentally different selectivity constraints from the numerous known synthetic methods that rely on substitution of a preexisting aromatic ring.
Why is this paper important? Firstly, the work is low-temperature, by the benefit of the catalyst. Also, phenols are the most important group of industrial chemicals. What this means for a company is that you can make more of a chemical, faster, cheaper and more efficiently. If I had money (well, some to spare) I would hedge on whomever licenses the patent for this work. I really applaude the authors for this phenomenally relevant work.
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