Affiliation:
1. Instituto de Química Departamento de Química Orgânica Universidade Federal do Rio Grande do Sul (UFRGS) P.O. Box 15003 Porto Alegre‐RS 91501‐970 Brazil
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.
Funder
Conselho Nacional de Desenvolvimento Científico e Tecnológico
Coordenação de Aperfeiçoamento de Pessoal de Nível Superior
Fundação de Amparo à Pesquisa do Estado do Rio Grande do Sul