Minisci C-H Alkylation of Heteroarenes Enabled by Dual Photoredox/Bromide Catalysis in Micellar Solutions

Santos, Marilia S. and Cybularczyk-Cecotka, Martyna and Koenig, Burkhard and Giedyk, Maciej (2020) Minisci C-H Alkylation of Heteroarenes Enabled by Dual Photoredox/Bromide Catalysis in Micellar Solutions. CHEMISTRY-A EUROPEAN JOURNAL, 26 (66). pp. 15323-15329. ISSN 0947-6539, 1521-3765

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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.

Item Type: Article
Uncontrolled Keywords: VISIBLE-LIGHT PHOTOREDOX; FREE-RADICAL REACTIONS; SELECTIVE ALKYLATION; HYDRATED ELECTRONS; HETEROCYCLES; ARYLATION; SECONDARY; BOND; FUNCTIONALIZATION; GENERATION; alkyl bromides; C-H functionalization; heteroarenes; micellar solution; photoredox catalysis
Subjects: 500 Science > 540 Chemistry & allied sciences
Divisions: Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Burkhard König
Depositing User: Dr. Gernot Deinzer
Date Deposited: 08 Mar 2021 13:36
Last Modified: 08 Mar 2021 13:36
URI: https://pred.uni-regensburg.de/id/eprint/43531

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