|
|||||
|
|
Minisci C?H Alkylation of Heteroarenes Enabled by Dual Photoredox/Bromide Catalysis in Micellar Solutions** |
|
| Authors: | Dr Marilia S Santos Dr Martyna Cybularczyk-Cecotka Prof Burkhard König Dr Maciej Giedyk |
| Institution: | 1. Institute of Organic Chemistry, Faculty of Chemistry and Pharmacy, University of Regensburg, Universitätsstraße 31, 93053 Regensburg, Germany
These authors contribute equally.;2. Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland These authors contribute equally.;3. Institute of Organic Chemistry, Faculty of Chemistry and Pharmacy, University of Regensburg, Universitätsstraße 31, 93053 Regensburg, Germany;4. Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland |
| Abstract: | Aromatic heterocycles are omnipresent structural motifs in various natural products, pharmaceuticals and agrochemicals. This work describes a photocatalytic Minisci-type C?H functionalization of heteroarenes with non-activated alkyl bromides. The reaction avoids stoichiometric radical-promoters, oxidants, or acids, and is conducted using blue LEDs as the light source. The reactive carbon-centered alkyl radicals are generated by merging the photoredox approach with bromide anion co-catalysis and spatial pre-aggregation of reacting species in the micellar aqueous solutions. The obtained data highlight the critical importance of microstructuring and organization of the components in the reaction mixture. |
| Keywords: | alkyl bromides C?H functionalization heteroarenes micellar solution photoredox catalysis |