Abstract
The oxidation of primary alcohols under mechanochemical conditions in a Spex8000M Mixer/Mill was investigated. To facilitate ease of separation and recyclability, a polystyrene-bound version of a TEMPO catalyst was employed. When paired with Oxone® in a stainless-steel vial with a stainless-steel ball, several primary alcohols were successfully oxidized to the corresponding carboxylic acids. The product was isolated using gravity filtration, which also allowed for the polystyrene-bound TEMPO catalyst to be recovered and reused in subsequent oxidation reactions. Furthermore, it was demonstrated that the size and steric hindrance of the primary alcohol does not hinder the rate of the reaction. Finally, the aldehyde was selectively obtained from a primary alcohol under ball milling conditions by using a combination of non-supported TEMPO with a copper vial and copper ball.
Highlights
The emerging field of mechanochemistry has garnered a lot of attention over the last few years [1,2,3,4,5,6,7,8]
We started our investigation by milling benzyl alcohol with 1 equivalent of PS-TEMPO in the
We started our investigation by milling benzyl alcohol with 1 equivalent of PS-TEMPO in the presence of 1 equivalent of Oxone®® for 16 h in a stainless-steel vial with a 3/16” stainless steel ball
Summary
The emerging field of mechanochemistry has garnered a lot of attention over the last few years [1,2,3,4,5,6,7,8]. The combination of mechanochemistry and polymer-supported catalysts will allow for the development of catalytic conditions that are new, solvent free and completely recyclable. Evenorganic though greenness category, indicating that there is still much work to be done in this area of green there are several alternatives to using toxic metals in the oxidation of alcohols to aldehydes, there are chemistry. Alcohol a metal-free variants in the literature, many use catalysts that are not commercially available and typically carboxylic acid. Oxone referred to as PS-TEMPO) in the presence of Oxone® under mechanochemical conditions would environmentally benign conditions reduce the use of undesired provide environmentally benign that conditions that reduce the solvents, use of chromatography-free, undesired solvents, metal-free, and recyclable for the oxidation of alcohols to carboxylic acids. Chromatography-free, metal-free, and recyclable for the oxidation of alcohols to carboxylic acids
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