Synthetic applications of carbamoyl radicals via photocatalysis

• Grant number: 17/02854-8
• Support Opportunities: Regular Research Grants
• Start date: May 01, 2017
• End date: 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)

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, JUL 16 2019. (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, OCT 16 2020. (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, JAN 19 2021. (18/07152-4, 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, JUL 28 2020. (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, OCT 2017. (14/13411-1, 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, JUL 2 2021. (17/02854-8, 19/24784-7, 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, APR 1 2020. (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, FEB 1 2021. (17/02854-8, 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., 2022-11-25. (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., 2017-10-01. (17/02854-8, 14/13411-1)