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

Author(s)

Santos, Marilia S. ^[1] ; Cybularczyk-Cecotka, Martyna ^[2] ; Koenig, Burkhard ^[1] ; Giedyk, Maciej ^[2]

Affiliation

^[1] Univ Regensburg, Fac Chem & Pharm, Univ Str 31, D-93053 Regensburg - Germany

^[2] Polish Acad Sci, Inst Organ Chem, Kasprzaka 44-52, PL-01224 Warsaw - Poland

• Document type: Journal article
• Source: CHEMISTRY-A EUROPEAN JOURNAL; v. 26, n. 66, p. 15323-15329, NOV 26 2020.
• Web of Science Citations: 0

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. (AU)

• FAPESP's process: 18/20956-5 - C-H Functionalization of Aliphatic and Aromatic Heterocycles by Visible Light Photoredox Catalysis
• Grantee: Marília Simão dos Santos
• Support Opportunities: Scholarships abroad - Research Internship - Post-doctor