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

preprint
revised on 23.06.2020 and posted on 25.06.2020 by Marila S. Santos, Martyna Cybularczyk-Cecotka, Burkhard Koenig, Maciej Giedyk
Microstructured aqueous solutions were employed to engage non-activated alkyl bromides in the visible-light-promoted C‑H functionalization of heteroarenes. The reactive carbon-centered alkyl radicals were generated by merging the photoredox approach, bromide anion co-catalysis and spatial pre-aggregation of reacting species in the mixture. The presented methodology allowed obtaining alkylated heteroarenes without stoichiometric radical-promoters, in acid-free conditions and using blue LEDs as the light source.

Funding

National Science Centre, Poland (SONATA 2018/31/D/ST5/00306)

Fundação de Amparo à Pesquisa do Estado de São Paulo – FAPESP (2018/20956-5 and 2017/03120-8)

German Science Foundation (DFG, KO 1537/18-1)

History

Email Address of Submitting Author

maciej.giedyk@icho.edu.pl

Institution

Institute of Organic Chemistry Polish Academy of Sciences

Country

Poland

ORCID For Submitting Author

0000-0002-7645-1356

Declaration of Conflict of Interest

There are no conflicts to declare

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