Abstract
The ability of triplet ketones to abstract a hydrogen atom from hydrocarbons is reminiscent of that of the high-spin metal-oxo complexes in C–H oxidation enzymes. In practice, the reactivity of triplet ketones is easier to control and applicable to promoting a wider range of reactions. We demonstrate herein the synthetic utility of triplet ketone-mediated C-addition of methanol to cyclopentenone derivatives with an expedient synthesis of the core skeleton of the [3 + 2]-type dimeric pyrrole–imidazole alkaloids. Remarkably, this photochemical C–H functionalization reaction is highly regioselective and can tolerate a good range of functional groups.
Original language | English (US) |
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Pages (from-to) | 769-772 |
Number of pages | 4 |
Journal | Tetrahedron |
DOIs | |
State | Published - Feb 22 2018 |
Keywords
- Conjugate addition
- C–H functionalization
- Photochemistry
- Radical reaction
- Triplet ketone
ASJC Scopus subject areas
- Biochemistry
- Drug Discovery
- Organic Chemistry