Abstract
A direct β-coupling of cyclic ketones with imines has been accomplished via the synergistic combination of photoredox catalysis and organocatalysis. Transient β-enaminyl radicals derived from ketones via enamine and oxidative photoredox catalysis readily combine with persistent α-amino radicals in a highly selective hetero radical-radical coupling. This novel pathway to γ-aminoketones is predicated upon the use of DABCO as both a base and an electron transfer agent. This protocol also formally allows for the direct synthesis of β-Mannich products via a chemoselective three-component coupling of aryl aldehydes, amines, and ketones.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 8404-8407 |
| Number of pages | 4 |
| Journal | Journal of the American Chemical Society |
| Volume | 137 |
| Issue number | 26 |
| DOIs | |
| State | Published - Jul 8 2015 |
All Science Journal Classification (ASJC) codes
- Catalysis
- Chemistry(all)
- Biochemistry
- Colloid and Surface Chemistry
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Jeffrey, J. L., Petronijević, F. R., & Macmillan, D. W. C. (2015). Selective Radical-Radical Cross-Couplings: Design of a Formal β-Mannich Reaction. Journal of the American Chemical Society, 137(26), 8404-8407. https://doi.org/10.1021/jacs.5b05376