Development of new synthetic methods in line with the green chemistry targeting complex molecules: multicomponent benzannulation, visible-light driven synthesis of dienes in presence of copper and preparation of bicyclic furan/8-membered ring ketones

• Grant number: 19/21506-6
• Support Opportunities: Regular Research Grants
• Start date: May 01, 2020
• End date: April 30, 2022
• Field of knowledge: Physical Sciences and Mathematics - Chemistry - Organic Chemistry
• Principal Investigator: Airton Goncalves Salles Junior
• Grantee: Airton Goncalves Salles Junior
• Host Institution: Instituto de Química (IQ). Universidade Estadual de Campinas (UNICAMP). Campinas , SP, Brazil

Abstract

The demands of the Green Chemistry approach bring about new challenges either in the academic environment or in industry. As Roger Sheldon stated, "Green Chemistry is primary pollution prevention rather than waste remediation", thus our chemical processes must be designed to be sustainable from the very beginning. Following all the principles of Green Chemistry is not easy at all; nevertheless, with the change in the mentality towards the planet's necessity and the perception of new opportunities created by this kind of Chemistry, a good prospect can be anticipated. Our group has been working on sustainable synthetic methods in such a way to be as close as possible to the principles of Green Chemistry. The background obtained so far allows us to embark in the development of methods targeting unprecedented complex molecules and yet to be "green". Our first proposal is a persulfate-promoted multicomponent benzannulation in water to have access to novel functionalized benzene rings. Functionalized benzenes are one of the most important classes of compounds in pharmaceuticals, natural products, functional organic materials and the most widely employed precursors in synthetic chemistry. As a second project, we intend to synthesize several complex dienes under visible-light photocatalysis in the presence of copper using the same starting materials of project 1. The third proposal is a base-promoted metal-free route in water toward unprecedented bicyclic furan/8-membered ring ketones. 8-membered rings are widely prevalent structures in natural products. However, their scarcity in marketed drug molecules supports the notion of how challenging is the synthesis of such moieties. In both proposals, the products obtained offer a wealth of opportunities for further functionalization. Mechanistic studies and multigram-scale preparation are planned for these transformations allowing a more fundamental investigation and testing the robustness of the protocols during the scale-up. Preliminary results for both proposals lend support to their viability. (AU)

Scientific publications

(References retrieved automatically from Web of Science and SciELO through information on FAPESP grants and their corresponding numbers as mentioned in the publications by the authors)

VON ZUBEN, THEODORA W.; SILVA, GUILHERME CARIELLO; SALLES JR, AIRTON G.. Visible light-driven metal-free synthesis of highly substituted pyrroles through C-H functionalisation. GREEN CHEMISTRY, v. 23, n. 17, AUG 2021. (19/21506-6)

SILVA, GUILHERME CARIELLO; DE SOUZA, GABRIELA F. P.; SALLES, AIRTON G., JR.. Catalytic redox-neutral C-H functionalisation with TEMPO in water to access aminomethyl-substituted pyrroles. ORGANIC & BIOMOLECULAR CHEMISTRY, v. 20, n. 17, p. 6-pg., 2022-04-11. (19/21506-6)

VON ZUBEN, THEODORA WROBEL; KALINKE, CRISTIANE; JANEGITZ, BRUNO CAMPOS; SALLES JR, AIRTON GONCALVES; BONACIN, JULIANO ALVES. 3D-printed amperometric sensor for the detection of ethanol in saliva. Electroanalysis, v. N/A, p. 11-pg., 2023-09-29. (21/07989-4, 19/21506-6, 13/22127-2, 19/00473-2)