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Synthetic applications of carbamoyl radicals via photocatalysis

Grant number: 17/02854-8
Support Opportunities:Regular Research Grants
Duration: May 01, 2017 - April 30, 2019
Field of knowledge:Physical Sciences and Mathematics - Chemistry - Organic Chemistry
Principal Investigator:Leandro Helgueira de Andrade
Grantee:Leandro Helgueira de Andrade
Host Institution: Instituto de Química (IQ). Universidade de São Paulo (USP). São Paulo , SP, Brazil

Abstract

Photochemistry is a growing field and has shown many interesting synthetic applications in recent years. In this work, we propose to investigate some radical reactions with formamides. Initially, we propose to carry out methodological studies to evaluate the addition of carbamoyl radicals to electron deficient olefins and aromatic compounds evaluating the scope and limitations of the methodology. In addition, we can apply the methodology to obtain important nitrogenous heterocyclic compounds. We also intend to investigate tandem radical addition / cyclization reactions with N-arylacrylamides with carbamoyl radicals for the synthesis of natural products, pyrroloindolines.Another study that we intend to explore with carbamoyl radicals is their use in the synthesis of new monomers, aiming the production of polymers. Therefore, our proposal is related to the preparation of a new series of amides (monomers) for their use in the enzymatic polymerization with di-amines and diols. To this end, photocatalytic amidations will be explored in order to obtain the desired monomers (amides). Then, By using enzymatic polymerization under continuous flow conditions we expect to produce the new polymers (polyesters and polyamides). (AU)

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Scientific publications (10)
(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)
SAIRE-SAIRE, SAMUEL; BARBOSA, EDUARDO C. M.; GARCIA, DANIEL; ANDRADE, LEANDRO H.; GARCIA-SEGURA, SERGI; CAMARGO, PEDRO H. C.; ALARCON, HUGO. Green synthesis of Au decorated CoFe2O4 nanoparticles for catalytic reduction of 4-nitrophenol and dimethylphenylsilane oxidation. RSC ADVANCES, v. 9, n. 38, p. 22116-22123, . (15/26308-7, 15/11452-5, 17/02854-8)
SANABRIA, MARIALY N.; HORNINK, MILENE M.; CORREIA, VALQUIRIA G.; ANDRADE, LEANDRO H.. Nontraditional Application of the Photo-Fenton Process: A Novel Strategy for Molecular Construction Using Formamide and Flow Chemistry. ORGANIC PROCESS RESEARCH & DEVELOPMENT, v. 24, n. 10, p. 2288-2297, . (19/10762-1, 17/02854-8)
NASCIMENTO, VINICIUS R.; SUENAGA, MELISSA L. S.; ANDRADE, LEANDRO H.. An efficient approach for the synthesis of new (+/-)-coixspirolactams. ORGANIC & BIOMOLECULAR CHEMISTRY, v. 18, n. 28, p. 5458-5465, . (19/10762-1, 17/02854-8)
HORNINK, MILENE MACEDO; LOPES, ALICE UVA; ANDRADE, LEANDRO HELGUEIRA. Biobased Spiroimides from Itaconic Acid and Formamides: Molecular Targets for a Novel Synthetic Application of Renewable Chemicals. SYNTHESIS-STUTTGART, v. 53, n. 02, p. 296-308, . (18/07152-4, 19/10762-1, 17/02854-8)
SASTRE, DIEGO E.; SANTOS, LEIDAIANY P.; KAGOHARA, EDNA; ANDRADE, LEANDRO H.. Draft Whole-Genome Sequence of Psychrotrophic Arthrobacter sp. Strain 7749, Isolated from Antarctic Marine Sediments with Applications in Enantioselective Alcohol Oxidation. MICROBIOLOGY RESOURCE ANNOUNCEMENTS, v. 5, n. 43, . (14/13411-1, 17/02854-8)
SANZ, CAROLINE G.; DIAS, KEVIN A.; BACIL, RAPHAEL P.; SERAFIM, RICARDO A. M.; ANDRADE, LEANDRO H.; FERREIRA, I, ELIZABETH; SERRANO, SILVIA H. P.. Electrochemical characterization of para- and meta-nitro substituents in aqueous media of new antichagasic pharmaceutical leaders. Electrochimica Acta, v. 368, . (17/02854-8, 19/10762-1)
SAIRE-SAIRE, SAMUEL; GARCIA-SEGURA, SERGI; LUYO, CLEMENTE; ANDRADE, LEANDRO H.; ALARCON, HUGO. Magnetic bio-nanocomposite catalysts of CoFe2O4/hydroxyapatite-lipase for enantioselective synthesis provide a framework for enzyme recovery and reuse. International Journal of Biological Macromolecules, v. 148, p. 284-291, . (17/02854-8)
SACCHELLI, BRUCE A. L.; ROCHA, BIANCA C.; ANDRADE, LEANDRO H.. Cascade Reactions Assisted by Microwave Irradiation: Ultrafast Construction of 2-Quinolinone-Fused gamma-Lactones from N-(o-Ethynylaryl)acrylamides and Formamide. ORGANIC LETTERS, v. 23, n. 13, p. 5071-5075, . (17/02854-8, 19/24784-7, 19/10762-1)
COUTO, JULIA L.; HORNINK, MILENE M.; NASCIMENTO, VINICIUS R.; ANDRADE, LEANDRO H.. Fast Transition Metal-Free Synthesis of Functionalized Oxindoles and Dihydroquinoline-2-ones Under Microwave Irradiation. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, v. 2022, n. 44, p. 10-pg., . (18/07152-4, 21/12555-3, 19/10762-1, 17/02854-8)
SASTRE, DIEGO E.; SANTOS, LEIDAIANY P.; KAGOHARA, EDNA; ANDRADE, LEANDRO H.. Draft Whole-Genome Sequence of Psychrotrophic Arthrobacter sp. Strain 7749, Isolated from Antarctic Marine Sediments with Applications in Enantioselective Alcohol Oxidation. GENOME ANNOUNCEMENTS, v. 5, n. 43, p. 2-pg., . (17/02854-8, 14/13411-1)

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