Development of new photochemical methodologies for the synthesis of small molecule and biomolecule modifications

• Grant number: 21/06099-5
• Support Opportunities: Regular Research Grants
• Start date: October 01, 2021
• End date: September 30, 2023
• Field of knowledge: Physical Sciences and Mathematics - Chemistry - Organic Chemistry
• Principal Investigator: Márcio Weber Paixão
• Grantee: Márcio Weber Paixão
• Host Institution: Centro de Ciências Exatas e de Tecnologia (CCET). Universidade Federal de São Carlos (UFSCAR). São Carlos , SP, Brazil

Abstract

In the last decades, the emphasis and application of sustainable chemistry principles have driven a change in behavior of both chemical industry and academy. They aim to obtain the desired product with fewest step, high yield and by using non-toxic reagents. In this context, the recognition of environmental benefits presented in photochemical reactions has motivated the scientific community to develop efficient and simple strategies for the synthesis of biologically relevant organic compounds.Consequently, this project aims the exploration of several synthetic methodologies promoted by visible light photoredox catalysis - wherein processes are mediated by transition metal complexes, photo-organocatalysts, photosensitizers and EDA complexes formation. In particular, photochemical procedures for incorporating carbon dioxide into complex molecular architectures through multicomponent reactions are highly desirable. Moreover, radical cascade reactions have been designed towards the synthesis of highly functionalized heterocyclic scaffolds (carboxylated and sulfonylated). Furthermore, photoredox strategies for the diffunctionalization of olefinic systems through multicomponent reactions. Besides, the reactivity of azametinoimines with carbamoyl and aryl radical species will be studied. These approaches should further be transferred to continuous flow regime, which will allow the scaling-up of the protocol.This project also intends the development of strategies for the synthesis of non-natural amino acids and peptide functionalization using photoredox catalysis. (AU)

Scientific publications

(11)

(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)

VEGA, KIMBERLY BENEDETTI; DELGADO, JOSE ANTONIO CAMPOS; PUGNAL, LUCAS V. B. L.; KOENIG, BURKHARD; CORREIA, JOSE TIAGO MENEZES; PAIXAO, MARCIO WEBER. Divergent Functionalization of Styrenes via Radical/Polar Crossover with CO₂ and Sodium Sulfinates. CHEMISTRY-A EUROPEAN JOURNAL, v. 29, n. 19, p. 9-pg., 2023-02-28. (21/06099-5, 21/01354-7, 19/01560-6, 17/10015-6)

PUGNAL, LUCAS V. B. L.; VEGA, KIMBERLY B.; PISSINATI, EMANUELE F.; CORREIA, JOSE TIAGO M.; ZUKERMAN-SCHPECTOR, JULIO; MARTIN, RUBEN; PAIXAO, MARCIO W.. 1,2-Arylsulfonylation of Vinyl Ethers and Esters Enabled by Dual Ni Catalysis. CHEMCATCHEM, v. N/A, p. 6-pg., 2023-06-19. (21/06099-5, 19/01560-6, 20/09353-7, 22/04597-0, 17/10015-6, 21/01354-7)

SOUZA, WANDERSON C.; CORREIA, JOSE TIAGO M.; MATOS, PRISCILLA M.; KISUKURI, CAMILA M.; CARNEIRO, PABLO S.; PAIXAO, MARCIO W.. Organophotocatalytic Intramolecular Formal Enyne-Metathesis - An Alternative to Transition-Metal Catalysis. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, v. 2022, n. 16, p. 5-pg., 2022-02-05. (21/06099-5, 17/10015-6, 14/50249-8, 20/00556-2)

DE SOUZA, WANDERSON C. C.; LIMA, RAFAELY N. N.; DE JESUS, IVA S. S.; CORREIA, JOSE TIAGO M.; PAIXAO, MARCIO W.. Synthesis of Benzoazepinone Derivatives via Photoredox Deaminative Radical Cascade Alkylation of 1,7-Dienes and 1,7-Enynes. SYNTHESIS-STUTTGART, v. N/A, p. 10-pg., 2022-12-20. (21/06099-5)

OLIVEIRA, PEDRO H. R.; TORDATO, EVERTON A.; VELEZ, JEIMY A. C.; CARNEIRO, PABLO S.; PAIXAO, MARCIO W.. Visible-Light Mediated Carbamoylation of Nitrones under a Continuous Flow Regime. Journal of Organic Chemistry, v. 88, n. 10, p. 13-pg., 2023-05-19. (21/06099-5)

JARDIM, GUILHERME A. M.; DANTAS, JULIANA A.; BARBOZA, AMANDA A.; PAIXAO, MARCIO W.; FERREIRA, MARCO A. B.. Light-Driven Palladium-Radical Hybrid Species: Mechanistic Aspects and Recent Examples. SYNTHESIS-STUTTGART, v. 54, n. 21, p. 17-pg., 2022-08-22. (20/10246-0, 20/01255-6, 21/06099-5)

MATSUO, BIANCA T.; OLIVEIRA, PEDRO H. R.; PISSINATI, EMANUELE F.; VEGA, KIMBERLY B.; DE JESUS, IVA S.; CORREIA, JOSE TIAGO M.; PAIXAO, MARCIO. Photoinduced carbamoylation reactions: unlocking new reactivities towards amide synthesis. CHEMICAL COMMUNICATIONS, v. 58, n. 60, p. 18-pg., 2022-07-07. (21/06099-5, 17/10015-6)

GONCALVES, RENAN. O.; OLIVEIRA, PEDRO H. R.; DE JESUS, IVA S.; DEBIA, NATALI P.; LUDTKE, DIOGO S.; PAIXAO, MARCIO W.. Synthesis of non-anomeric C-glycosyl pyrazolidinone derivatives via visible-light photoredox catalysis. ORGANIC & BIOMOLECULAR CHEMISTRY, v. 21, n. 27, p. 5-pg., 2023-06-14. (21/06099-5)

PISSINATI, EMANUELE F.; DELGADO, JOSE A. C.; MORO, PEDRO A. M.; CORREIA, JOSE T. M.; BERLINCK, ROBERTO G. S.; PAIXAO, MARCIO W.. Expanding the Chemical Space of Non-Proteinogenic N-4-Substituted Asparagine: Racemic, Enantioenriched, and Deuterated Derivatives. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, v. 26, n. 21, p. 7-pg., 2023-05-17. (17/10015-6, 15/01017-0, 21/06099-5, 19/17721-9)

CONCEPCION, ODETTE; PENALOZA, FRANCISCO J.; LOPEZ, JHON JAIRO; CABRERA-BARJAS, GUSTAVO; JIMENEZ, CLAUDIO A.; PAIXAO, MARCIO W.; DE LA TORRE, ALEXANDER F.. Ugi and Passerini reactions enable the incorporation of Delta AA into N-alkylated peptides and depsipeptides. NEW JOURNAL OF CHEMISTRY, v. 46, n. 24, p. 8-pg., 2022-05-12. (21/06099-5)

VASCONCELOS, SANCLER C.; MARCHINI, LUCAS; LIMA, CAROLINA G. S.; MADRIAGA, VINICIUS G. C.; RIBEIRO, RUAN S. A.; ROSSA, VINICIUS; FERREIRA, LUANNE E. M.; DA SILVA, FERNANDO DE C.; FERREIRA, VITOR F.; PASSOS, FABIO BARBOZA; et al. Single-atom catalysts for the upgrading of biomass-derived molecules: an overview of their preparation, properties and applications. GREEN CHEMISTRY, v. 24, n. 7, p. 30-pg., 2022-02-28. (21/06099-5, 14/50249-8)