Categories: C-H Bond Formation >
Deoxygenations of phenols
A mild, versatile, Pd/C-catalyzed deoxygenation of phenolic hydroxyl groups via aryl triflates or mesylates using Mg metal in MeOH at room temperature was developed. The addition of NH4OAc dramatically affects the reactivity and reaction rate.
H. Sajiki, A. Mori, T. Mizusaki, T. Ikawa, T. Meagazwa, K. Hirota, Org. Lett., 2006, 8, 987-990.
Nickel-on-graphite is a very inexpensive, heterogeneous catalyst for the chemoselective reduction of aryl tosylates and mesylates. The catalyst can be used under conventional heating conditions or microwave irradiation and is recyclable without loss of activity.
B. H. Lipshutz, B. A. Frieman, T. Butler, V. Kogan, Angew. Chem. Int. Ed., 2006, 45, 800-803.
A nickel-catalyzed hydrodeoxygenation of aryl sulfamates enables the use of alcohols as mild reductants. A variety of functional groups and heterocycles were tolerated in this reaction system to give the desired products in high yields.
K. Matsuo, M. Kuriyama, K. Yamamoto, Y. Demizu, K. Nishida, O. Onomura, Synthesis, 2021, 53, 4449-4460.