Palladium-Catalyzed Carbonylative Cyclization of 1-Alkynyl-2-iodo-<scp>d</scp>-glucal
Cascade reactions are important synthetic tools for the synthesis of heterocyclic molecules, particularly those catalyzed by palladium. Herein, we report a palladium-catalyzed aminocarbonylative cyclization of new 1-alkynyl-2-iodo-d-glucals, which undergo a tandem carbonylative cyclization in the presence of various amine nucleophiles. A broad range of aromatic and aliphatic amines were applied as coupling partners, resulting in the selective and high-yield synthesis of glycosides fused to pyridinones. A plausible mechanism is proposed, proceeding via a tandem palladium aminocarbonylation followed by a palladium-catalyzed <i>endo-dig</i> cyclization.
Authors
- Milene M. Hornink (ORCID: https://orcid.org/0000-0002-6832-7259)
- Hélio A. Stefani (ORCID: https://orcid.org/0000-0002-7805-2834)
- Mônica F. Z. J. Toledo (ORCID: https://orcid.org/0000-0001-7974-4480)
- Daniel Carvalho Pimenta (ORCID: https://orcid.org/0000-0003-2406-0860)
- Giuseppe E. Figlino
Institutions
- Universidade de São Paulo (BR)
- Instituto Butantan (BR)
- Centro Universitário São Camilo (BR)
Publication Details
- Journal
- Organic Letters
- Published
- 2024-09-30
- DOI
- https://doi.org/10.1021/acs.orglett.4c03337
- Primary Topic
- Catalytic Cross-Coupling Reactions
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- Fundação de Amparo à Pesquisa do Estado de São Paulo
- Coordenação de Aperfeiçoamento de Pessoal de Nível Superior
- Conselho Nacional de Desenvolvimento Científico e Tecnológico
- Financiadora de Estudos e Projetos