Work

Selective Ruthenium‐Catalyzed Photoredox α‐C(sp3)–H Alkynylation of Cyclic Amines under Visible Light

Year: 2025

Type: article

Abstract: A direct visible‐light α‐C(sp3)–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]Cl2·6H2O as a photocatalyst, driven by blue LED (455 nm) irradiation. Detailed mechanistic studies and cyclic voltammetry support the proposed reaction pathway, where the C(sp3)–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.

Source: European Journal of Organic Chemistry

DOI: 10.1002/ejoc.202500254

Authors: Caren D. G. Silva, Douglas B. Paixão, Eduardo G. O. Soares, Paulo H. Schneider

Institutions: Universidade Federal do Rio Grande do Sul, Universidade Federal do Rio Grande

Language: English

Topic: Radical Photochemical Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $4,330

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