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PhSeZn-halides are the first class of bench stable nucleophilicorganoselenium reagents. Discovered in 2008, these compounds can be easily prepared from PhSeBr and PhSeCl by oxidative insertion of the elemental zinc in refluxing tetrahydrofurane and purified by crystalization from diethyl ether or heptane. The nucleophilicity of these reagents showed an important rate acceleration when effected in "on water" conditions contributing to enhance the greenest of the nucleophilic selenenylation reactions. PhSeZnCl and PhSeZnBr are unusually stable slenolates in which the selenium atom have the same oxidation state that in the redox enzyme Glutathione Peroxidase (GPx). This confer to these molecules an important GPx-like activity associated to a strong antioxidant property.
^Santi, Claudio; Santoro, Stefano; Battistelli, Benedetta; Testaferri, Lorenzo; Tiecco, Marcello (1 November 2008). "Preparation of the First Bench-Stable Phenyl Selenolate: an Interesting "On Water" Nucleophilic Reagent". European Journal of Organic Chemistry2008 (32): 5387–5390. doi:10.1002/ejoc.200800869.