Oxidative cleavage of olefins is a powerful synthetic method for producing a range of desired organic compounds and is often used, for example, by the pharmaceutical industry and the petroleum industry. Current methods rely on oxidants, such as potassium permanganate and sodium periodate, or ozonolysis. There are serious drawbacks to these methods such as solubility issues, undesirable side-products, poor yields, and, in the case of ozonolysis, production of explosive intermediates.
Description of Technology
This invention provides a mild, safe and versatile method of oxidatively cleaving mono, 1,1-di, 1,2-di, tri, or tetra substituted olefins using an osmium tetraoxide catalyst and Oxone®, as the oxidant, to selectively produce aldehydes, ketones, carboxylic acids, or esters.
- Efficient: The method tolerates many types of functionalities and selectively produces desired oxidation state (i.e. products) upon a simple change in solvent. The osmium tetraoxide catalyst displays a high degree of turnover and can be easily recovered if bound to a polymer support. Oxone® is inexpensive, environmentally friendly and easy to handle.
- Safe: There is no production of highly explosive ozonide intermediates.
- Facile: The reactions can be run at a variety of temperatures with no degradation of catalyst, oxidant, or products. All reaction species are commercially available and the reaction can be run in existing facilities.
This application could supplement or replace ozonolysis in the petroleum industry, the pharmaceutical industry, and the paper industry, all of which utilize ozonolysis to produce their products. This can also replace current oxidation procedures used in the chemical industry and custom synthesis and active pharmaceutical ingredients suppliers.
US 6,787,671 (issued Sep. 7, 2004)
Babak Borhan, Benjamin Travis, Jennifer Schomaker