Isochromene and Dihydroisobenzofuran Electrosynthesis by a Highly Regiodivergent Cyclization of 2-Ethynylbenzaldehydes
The synthesis of isochromene and dihydroisobenzofuran compounds is presented through the electrochemical cyclization of 2-ethynylbenzaldehydes using silver as a sacrificial electrode. The results demonstrate exceptional regiodivergency, without the use of external oxidants or transition metal catalysts, with products reaching up to 97% isolated yield. Density functional theory (DFT) studies, along with control experiments, were conducted to elucidate a plausible reaction mechanism.
Authors
- Kléber T. de Oliveira (ORCID: https://orcid.org/0000-0002-9131-4800)
- Guilherme M. Martins (ORCID: https://orcid.org/0000-0002-0493-1270)
- Pedro P. de Castro (ORCID: https://orcid.org/0000-0002-3018-3130)
- Samuel R. Mendes (ORCID: https://orcid.org/0000-0002-2388-3008)
- Timothy J. Brocksom (ORCID: https://orcid.org/0000-0003-2215-0248)
- Guilherme B. Simoso
- Felipe de Lucca
Institutions
- Universidade Federal de Juiz de Fora (BR)
- Universidade do Estado de Santa Catarina (BR)
- Universidade Federal de São Carlos (BR)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2025-06-30
- DOI
- https://doi.org/10.1021/acs.joc.5c00967
- Citations
- 1
- Primary Topic
- Oxidative Organic Chemistry Reactions
- Type
- article
- Field-Weighted Citation Impact
- 0.94
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
- Fundação de Amparo à Pesquisa do Estado de Minas Gerais
- Fundação de Amparo à Pesquisa e Inovação do Estado de Santa Catarina