Samarium diiodide (SmI2) is a versatile single-electron reductant which can reduce various functional groups under mild reaction conditions and facilitate radical and nucleophilic carbon-carbon bond-forming events. It was realized as a synthetic tool in the early 1980’s, and since then various studies have been carried out to understand the types of functional groups SmI2 can reduce, as well as the rates at which these reductions take place.

SmI2 behaves as a reductant in its +2 oxidation state, and when it is exposed to air it is rapidly oxidized to its non-reactive +3 oxidation state. This air-sensitivity is easily managed by carrying out SmI2 reactions under inert Argon atmosphere. In industry and many large universities gloveboxes can be used with SmI2 as a reagent with reasonable ease; however, many labs do not have this equipment. While it ranks as one of the top synthetic tools to organic chemists, if research chemists are intimidated by its need for specialized equipment the reagent will become underutilized. For this reason, one of the goals of many of the top SmI2 researchers is to make it clear to the researching public the ease of SmI2 use in the lab. This becomes an even larger hurdle when working in primary undergraduate institutions, where inert atmosphere equipment, like a glovebox, may not be standard.

A lower cost alternative to a glovebox is access to a vacuum pump, argon tank and Schlenck line glassware. The goal in our lab is to work through the details of the synthesis, identify the most important factors and write a protocol for the formation and use of SmI2 using a Schlenck line oxygen-free technique. The only way that SmI2 can become a more common reagent with synthetic chemists is to communicate how everyone can use this reagent properly even without more sophisticated equipment.