Scalable and safe synthetic organic electroreduction inspired by Li-ion battery chemistry

Reductive electrosynthesis has faced long-standing challenges in applications to complex organic substrates at scale. Here, we show how decades of research in lithium-ion battery materials, electrolytes, and additives can serve as an inspiration for achieving practically scalable reductive electrosynthetic conditions for the Birch reduction. Specifically, we demonstrate that using a sacrificial anode material (magnesium or aluminum), combined with a cheap, nontoxic, and water-soluble proton source (dimethylurea), and an overcharge protectant inspired by battery technology [tris(pyrrolidino)phosphoramide] can allow for multigram-scale synthesis of pharmaceutically relevant building blocks. We show how these conditions have a very high level of functional-group tolerance relative to classical electrochemical and chemical dissolving-metal reductions. Finally, we demonstrate that the same electrochemical conditions can be applied to other dissolving metal–type reductive transformations, including McMurry couplings, reductive ketone deoxygenations, and epoxide openings.

Source: ScienceNOW - February 21, 2019 Category: Science Authors: Peters, B. K., Rodriguez, K. X., Reisberg, S. H., Beil, S. B., Hickey, D. P., Kawamata, Y., Collins, M., Starr, J., Chen, L., Udyavara, S., Klunder, K., Gorey, T. J., Anderson, S. L., Neurock, M., Minteer, S. D., Baran, P. S. Tags: Chemistry r-articles Source Type: news