General approach to photocatalytic activation of inactivated alkyl halides

For many years, humans have been trying to emulate nature and harness the power of the sun for everything we can imagine- including synthetic chemistry and the generation of reactive organic molecules, even radical fragments. Radicals have a remarkable ability to add to alkenes with very small reaction barriers- provided the electronics of the alkene and radical match. The generation of the alkyl radical component, on the other hand, has traditionally relied on the use of toxic tin salts as well as deep UV light which substantially diminishes enthusiasm for this remarkable coupling reaction. Some of the challenges associated with this reaction stem from the use of the alkyl iodide precursors which are somewhat operationally limited, as well as the use of deep UV light, which substantially limits the use of the functionally rich substrates. In our efforts, we have shown that visible light can be used to convert the synthetically more accessible alkyl chlorides and bromides into radicals capable of undergoing highly efficient additions to aα, β-unsaturated alkenes in excellent yields without the use of toxic salts. Specifically, this poster will discuss the optimization of secondary chlorides with benzyl acrylates.