Selective Ruthenium‐Catalyzed Photoredox α‐C(sp<sup>3</sup>)–H Alkynylation of Cyclic Amines under Visible Light
A direct visible‐light α‐C( sp 3 )–H bond alkynylation of N ‐aryl pyrrolidine derivatives with 1‐bromoalkynes has been developed, enabling the synthesis of propargylic amines. This transformation utilizes [Ru(bpy) 3 ]Cl 2 ·6H 2 O as a photocatalyst, driven by blue LED (455 nm) irradiation. Detailed mechanistic studies and cyclic voltammetry support the proposed reaction pathway, where the C( sp 3 )–C( sp ) bond formation occurs via the oxidation of α‐amino radicals, followed by a radical coupling with 1‐bromoalkynes. This approach offers a straightforward, efficient, and selective method for synthesizing a wide range of cyclic α‐aminoalkynes, yielding moderate to good yields.
Authors
- Paulo H. Schneider (ORCID: https://orcid.org/0000-0003-4082-7152)
- Douglas B. Paixão
- Caren D. G. Silva (ORCID: https://orcid.org/0000-0001-6856-4660)
- Eduardo G. O. Soares
Institutions
- Universidade Federal do Rio Grande (BR)
- Universidade Federal do Rio Grande do Sul (BR)
- University of Rio Grande and Rio Grande Community College (US)
Publication Details
- Journal
- European Journal of Organic Chemistry
- Published
- 2025-06-13
- DOI
- https://doi.org/10.1002/ejoc.202500254
- Citations
- 1
- Primary Topic
- Catalytic C–H Functionalization Methods
- Type
- article
- Field-Weighted Citation Impact
- 0.94
Funders
- Coordenação de Aperfeiçoamento de Pessoal de Nível Superior
- Conselho Nacional de Desenvolvimento Científico e Tecnológico
- Fundação de Amparo à Pesquisa do Estado do Rio Grande do Sul