Details

Autor(en) / Beteiligte

• Cole, Justin P
• Chen, Dian-Feng
• Kudisch, Max
• Pearson, Ryan M
• Lim, Chern-Hooi
• Miyake, Garret M

Titel

Organocatalyzed Birch Reduction Driven by Visible Light

Ist Teil von

• Journal of the American Chemical Society, 2020-08, Vol.142 (31), p.13573-13581

Ort / Verlag

United States: American Chemical Society

Erscheinungsjahr

2020

Link zum Volltext

Quelle

MEDLINE

Beschreibungen/Notizen

• 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. Birch reductions traditionally employ alkali metals dissolved in ammonia to produce a solvated electron for the reduction of unactivated arenes such as benzene (E red < −3.42 V vs SCE). Photoredox catalysts have been gaining popularity in highly reducing applications, but none have been reported to demonstrate reduction potentials powerful enough to reduce benzene. Here, we introduce benzo­[ghi]­perylene imides as new organic photoredox catalysts for Birch reductions performed at ambient temperature and driven by visible light from commercially available LEDs. Using low catalyst loadings (<1 mol percent), benzene and other functionalized arenes were selectively transformed to 1,4-cyclohexadienes in moderate to good yields in a completely metal-free reaction. 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.