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8.1 Recent Developments in Catalytic Alcohol Oxidation Using Nitroxyl Radicals

DOI: 10.1055/sos-SD-225-00270

Dornan, L. M.; Hughes, N. L.; Muldoon, M. J.Science of Synthesis: Catalytic Oxidation in Organic Synthesis, (20171529.

General Introduction

Although there are many methods for oxidizing alcohols on a small laboratory scale, many of these methods are problematic for larger-scale industrial application due to safety and environmental concerns.[‌1‌] For example, the use of stoichiometric chromium reagents is very undesirable. In the last 10 to 20 years, there has been a growing momentum in academic efforts to develop catalytic methods for the oxidation of alcohols.[‌2‌] There are a now a wide variety of methods that utilize a range of transition metals, enzymes, and organocatalysts as catalysts and employ a number of different terminal oxidants. In this chapter, we will focus on the use of nitroxyl radical based catalysts. Catalytic methods using this class of radicals have evolved in the last 10 years, and they have a number of advantages over many of the alternatives. For example, nitroxyl-based systems have superior substrate scope/functional-group tolerance compared to precious-metal catalysts. In the case of some industrial applications, the avoidance of precious metals is also an advantage from a cost and toxicity point of view.

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References