Light-Activated Approaches to Highly Challenging Organic Electron Transfer Reactions

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Reduction and oxidation are central to chemistry and biology and relate to the addition of electrons or the removal of electrons from substances. Until now, many important but difficult reductions have only been accomplished with very powerful metal reducing agents, like sodium, but we have recently discovered simple neutral organic compounds, composed exclusively of the plentiful elements carbon, hydrogen and nitrogen, that act as powerful reducing agents. In 2012, we found that these substances become even more powerful reducing agents when irradiated with ultra-violet light and are even able to donate electrons to benzene rings that contain no significant electron-withdrawing groups. We now propose to develop this approach to determine the scope of the chemistry, using visible light to trigger the reactions, rather than untraviolet light, and converting our transformations it into protocols that use our electron donors catalytically.We believe that the principal reactions that are currently undertaken by sodium dissolved in liquid ammonia can be undertaken by our reagents in organic solvent and irradiated with light. This will not only add economic benefit through use of catalytic processes, but also convenience and enhancements in safety through avoiding reactive species like sodium that are hazardous both to use and to transport.