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Organocatalyzed Birch Reduction Driven by Visible Light

preprint
submitted on 17.02.2020 and posted on 19.02.2020 by Justin P. Cole, Dian-Feng Chen, Max Kudisch, Ryan M. Pearson, Chern-Hooi Lim, Garret Miyake

The Birch reduction is a powerful synthetic methodology that uses solvated electrons to convert inert arenes to 1,4-cyclohexadienes—valuable intermediates for building molecular complexity. This reaction historically requires dangerous alkali metals and cryogenic liquid ammonia as the solvent, severely limiting application potential and scalability. Here, we introduce benzo[ghi]perylene imides as new organic photoredox catalysts for Birch reductions performed at ambient temperature and driven by visible light. Using low catalyst loadings (<1 mole percent), benzene and other functionalized arenes can be selectively transformed to 1,4-cyclohexadienes in good yields. Mechanistic studies support that this unprecedented visible light induced reactivity is enabled by the ability of the organic photoredox catalyst to harness the energy from two visible light photons to affect a single, high energy chemical transformation, likely proceeding through a solvated electron.

History

Email Address of Submitting Author

garret.miyake@colostate.edu

Institution

Colorado State University

Country

United States

ORCID For Submitting Author

0000-0003-2451-7090

Declaration of Conflict of Interest

No conflict of interest

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in Journal of the American Chemical Society

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