Greening the Synthesis of 2,3‐Dihydrobenzofuran Selenides: I<sub>2</sub>/TBHP‐Promoted Selenocyclization of 2‐Allylphenols
Abstract In this work we describe the synthesis of selenium‐containing dihydrobenzofurans through the selenocyclization reaction of 2‐allylphenols. The reaction procedure uses only an I 2 /TBHP oxidant system at room temperature, enabling an efficient synthesis of 2‐[(organoselanyl)methyl]‐2,3‐dihydrobenzofurans. The products are formed immediately after the addition of the oxidant system in a mixture of 2‐allylphenol and diorganyl diselenide, in the absence of solvent, at mild experimental conditions. Furthermore, control experiments were carried out, including 77 Se NMR analyses to identify intermediates, which contributed to the elucidation of the reaction mechanism.
Authors
- Raquel G. Jacob (ORCID: https://orcid.org/0000-0001-9603-3795)
- Ricardo H. Bartz (ORCID: https://orcid.org/0000-0003-4269-3389)
- Gelson Perin (ORCID: https://orcid.org/0000-0003-0359-0811)
- Paulo Sérgio Lopes de Souza (ORCID: https://orcid.org/0000-0002-1560-2704)
- Márcio S. Silva (ORCID: https://orcid.org/0000-0002-7606-564X)
- Paola S. Hellwig (ORCID: https://orcid.org/0000-0002-6087-707X)
- Lucas E. B. Iarocz (ORCID: https://orcid.org/0000-0003-1920-302X)
- Eder J. Lenardão (ORCID: https://orcid.org/0000-0001-7920-3289)
Institutions
- Universidade Federal de Pelotas (BR)
Publication Details
- Journal
- European Journal of Organic Chemistry
- Published
- 2024-12-29
- DOI
- https://doi.org/10.1002/ejoc.202401243
- Citations
- 8
- Primary Topic
- Organoselenium and organotellurium chemistry
- Type
- article
- Field-Weighted Citation Impact
- 2.81
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
- Financiadora de Estudos e Projetos