The responsibility of today's chemists to develop chemical reactions that are not only highly efficient but also consistent with green chemistry guidelines is undeniable. The construction of complex molecules out of smaller, more easily available molecules ("building blocks") is an important goal in synthetic organic chemistry. Physiologically active natural and non-natural products that can be used for treatment of human disease are frequently the target of efforts in organic synthesis. In order to be environmentally conscious and applicable to industry-scale production, syntheses of these products have to be as concise and reliable as possible, generating a minimum of waste or hazardous by-products. Therefore, the discovery of new transformations and reactions that fulfill these requirements is a primary objective of synthetic chemistry. Catalytic reactions involving transition metals are strong candidates for this effort, as by definition the catalyst is regenerated at the end of the reaction and can thus potentially be re-used. This minimizes the amount of hazardous waste produced and states an important green chemistry principle. Not surprisingly, metal-catalyzed processes have already found broad use in industrial production of chemicals. We are investigating new pathways to use transition metals as a means to generate synthetic building blocks. One way is to develop methods to functionalize alkenes (readily available from petrochemicals), which leads to compounds with increased value and versatility. Our approach to this task is to oxidatively transform the alkene into a species known as a 2-metallaoxetane. The oxidant is hydrogen peroxide which has already found wide use in ecologically relevant applications as it is environmentally benign and the only by-product generated is water.
We are investigating the reactivity of these compounds by exposing them to different reaction conditions such as organometallic reagents to obtain functionalized products.
The ongoing research is a fundamentally new approach to the functionalization of alkenes and has many potential applications for the synthetic chemistry community. Moreover the reactions being studied have the potential to render important synthetic building blocks with high efficiency and low environmental impact by using benign reactants.