Mechanochemistry has emerged as an attractive technique for transition-metal catalyzed organic transformations. Many of these reactions have been performed in a solventless environment under high-speed ball milling conditions with the catalysts that would normally be used for solvent-based methods. However, solvent is not required for high-speed ball milling, so alternatives to these typical catalysts have been explored. For example, reactions like Sonogashira and Copper Azide-Alkyne Cycloaddition reactions that typically employ a CuI catalyst can be realized using just a metallic form of copper, like foil, pellets, or the reaction vial itself. Being able to use materials like these for metal-mediated reactions opens new opportunities for more inexpensive and reusable catalysts and reagents. One type of reaction that uses metal in this way and shows potential to a create a variety of different products is the mechanochemical reduction of carbonyl groups by single electron transfer (SET) reagents. We have shown that stainless steel containing Ni, Fe, and Cr may be used as the single electron transfer reagent to reduce aldehydes to their corresponding alcohols in the presence of water. Tangential experiments to this one suggests that deoxygenation of aldehydes may also be an efficient process by using a combination of the metals from stainless steel. This presentation will focus on the variety of pathways that occur from metal-mediated SET reactions under mechanochemical conditions just by changing the overall temperature of the reaction vial, the amount of water used, and the polarity of the reaction environment.

Tuning the potential: Stainless steel as an effective reducing agent for mechanochemical reactions

2019 Spring National Meeting

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