Oxidation of aliphatic C-H bonds catalyzed by transition metals

• Grant number: 18/04837-6
• Support Opportunities: Research Grants - Young Investigators Grants
• Start date: September 01, 2018
• End date: August 31, 2024
• Field of knowledge: Physical Sciences and Mathematics - Chemistry - Organic Chemistry
• Principal Investigator: Emílio Carlos de Lucca Júnior
• Grantee: Emílio Carlos de Lucca Júnior
• Host Institution: Instituto de Química (IQ). Universidade Estadual de Campinas (UNICAMP). Campinas , SP, Brazil
• Associated scholarship(s): 23/13162-0 - Synthesis of natural di- and triterpenes through selective oxidation reactions of C-H bonds, BP.DD; 23/06648-4 - Studies on the synthesis of pimaranes from labdanes and application in the synthesis of natural products, BP.IC; 23/03033-9 - Selective late-stage oxidation of C-H bonds in the synthesis of complex natural diterpenes, BP.DD; + associated scholarships 22/03331-7 - Synthesis of natural diterpenes through oxidation reactions of C-H bonds, BP.IC; 21/07167-4 - On the search of a new catalysts for oxidation reactions of C-H bonds, BP.DD; 21/01918-8 - Late-stage C-H functionalization: using the position C19 of steviol as a directing group, BP.IC; 20/11568-1 - Development of a catalytic system compatible with olefins and aromatic systems for oxidation of C-H bonds, BP.MS; 19/27528-1 - The development of a catalytic system that avoids the oxidation of alcohols to the corresponding carbonyl compounds, BP.DD; 19/09298-9 - Chemselective oxidations of aliphatic C-H bonds in aromatic compounds catalyzed by transition metals, BP.IC - associated scholarships

Abstract

The traditional applied methods for construction and growth of complexity in organic molecules rely on the manipulation of functional groups which are considered reactive, such as, carbonyls, alcohols, amines, and halogenated groups. In contrast, nature routinely uses methods to direct oxidation of C-H bonds, installing oxidized functionalities directly onto complex hydrocarbon framework, without pre-functionalization. Thus, the development of catalytic methods for the oxidation of C-H bonds presents a series of advantages, such as, the increase of synthetic efficiency. Despite the advances made, in order to the C-H bond oxidation reaches its full potential, a series of challenges still have to be overcome and, therefore, we propose to investigate catalytic systems to develop reactions: 1) compatible with electron-rich functional groups, i.e., olefins and aromatic rings. 2) to avoid oxidation of alcohols to the corresponding carbonyl compound. 3) which oxidize methyl groups to the corresponding alcohols and/or carboxylic acids. (AU)

Scientific publications

(4)

(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)

EDUARDO C. S. ROCHA; YASMIN N. SALMAZO; MARCIO HAYASHI; CÉSAR A. D. ZARAGOZA; EMILIO C. DE LUCCA JÚNIOR. FUNCIONALIZAÇÃO DE LIGAÇÕES C—H EM ESTÁGIO TARDIO EM SÍNTESE ORGÂNICA. Química Nova, v. 46, n. 1, p. 43-76, 2023-03-03. (18/04837-6, 21/01918-8)

ROCHA, EDUARDO C. S.; SALMAZO, YASMIN N.; HAYASHI, MARCIO; ZARAGOZA, CESAR A. D.; DE LUCCA, EMILIO C.. LATE-STAGE FUNCTIONALIZATION OF C-H BONDS IN ORGANIC SYNTHESIS. Química Nova, v. N/A, p. 34-pg., 2022-09-13. (18/04837-6, 21/01918-8)

SANTANA, VICTOR C. S.; FERNANDES, MILENA C., V; CAPPUCCELLI, ISADORA; RICHIERI, ANA CAROLINA G.; DE LUCCA JR, EMILIO C.. Metal-Catalyzed C-H Bond Oxidation in the Total Synthesis of Natural and Unnatural Products. SYNTHESIS-STUTTGART, v. 54, n. 24, p. 23-pg., 2022-10-06. (18/04837-6, 19/27528-1, 21/07167-4)

SANTANA, VICTOR C. S.; ROCHA, EDUARDO C. S.; PAVAN, JULIAN C. S.; HELENO, VLADIMIR C. G.; DE LUCCA JR, EMILIO C.. Selective Oxidations in the Synthesis of Complex Natural ent-Kauranes and ent-Beyeranes. Journal of Organic Chemistry, v. N/A, p. 5-pg., 2022-07-21. (18/04837-6, 21/01918-8, 19/27528-1)