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Professor Shannon Stahl

The Stahl Lab focuses on the development of catalysts and catalytic reactions for selective oxidation of organic molecules, with particular emphasis on aerobic oxidation reactions.

The Cu/TEMPO and Cu/ABNO catalysts for aerobic oxidation of alcohols to aldehydes and ketones are highly practical: they exhibit chemoselectivity and functional-group tolerance that is unmatched, even by many widely used stoichiometric oxidants, such as chromium oxide and hypervalent iodine species. They often operate efficiently at room temperature with ambient air as the oxidant, and the product is often able to be used directly in subsequent reactions, with no purification or following filtration through a plug of silica gel.

Other methods of interest include Cu/ABNO-catalyzed amine oxidation, including conversion of primary amines or nitriles, Cu/TEMPO- and Cu/ABNO-catalyzed oxidative coupling of primary alcohols and ammonia to nitriles, ortho-quinone-catalyzed oxidation of amines to imines and dehydrogenation of saturated nitrogen heterocycles to cyclic imines or aromatic heterocycles.

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Alison E Wendlandt, Shannon S Stahl
Journal of the American Chemical Society 2014-08-27
Quinolines are common pharmacophores present in numerous FDA-approved pharmaceuticals and other bioactive compounds. Here, we report the design and development of new o-quinone-based catalysts for the oxidative dehydrogenation of tetrahydroquinolines to afford quinolines. Use of a Co(salophen) cocatalyst allows the reaction to p...Read More
Janelle E Steves, Shannon S Stahl
Journal of the American Chemical Society 2013-10-23
Cu/TEMPO catalyst systems promote efficient aerobic oxidation of sterically unhindered primary alcohols and electronically activated substrates, but they show reduced reactivity with aliphatic and secondary alcohols. Here, we report a catalyst system, consisting of ((MeO)bpy)Cu(I)(OTf) and ABNO ((MeO)bpy = 4,4'-dimethoxy-2,2'-bi...Read More
Jessica M Hoover, Shannon S Stahl
Journal of the American Chemical Society 2011-10-26
Aerobic oxidation reactions have been the focus of considerable attention, but their use in mainstream organic chemistry has been constrained by limitations in their synthetic scope and by practical factors, such as the use of pure O(2) as the oxidant or complex catalyst synthesis. Here, we report a new (bpy)Cu(I)/TEMPO catalyst...Read More
A P Baturo, M B Lifshits, V P Raginskaia, E E Romanenko, E V Kholodkova
Khirurgiia 1976-12-01