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

Byron K. Peters, Kevin X. Rodriguez, Solomon H. Reisberg, Sebastian B. Beil, David P. Hickey, Yu Kawamata, Michael Collins, Jeremy Starr, Longrui Chen, Sagar Udyavara, Kevin Klunder, Timothy J. Gorey, Scott L. Anderson, Matthew Neurock, Shelley D. Minteer, Phil S. Baran

Research output: Contribution to journalArticlepeer-review

64 Scopus citations

Abstract

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.

Original languageEnglish (US)
Pages (from-to)838-845
Number of pages8
JournalScience
Volume363
Issue number6429
DOIs
StatePublished - 2019

Bibliographical note

Funding Information:
Financial support for this work was provided by NSF (CCI Phase 1 grant 1740656) to M.N., S.D.M., and P.S.B. Financial support was also provided by Pfizer and Asymchem. B.K.P. and K.X.R. acknowledge the Swedish Research Council (Vetenskapsrådet, VR 2017-00362) and National Institutes of Health (PA-18-586), respectively, for funding their postdoc fellowships. Y.K. acknowledges the Hewitt Foundation for a postdoctoral fellowship. S.H.R. acknowledges an NSF GRFP (#2017237151) and a Donald and Delia Baxter Fellowship.

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