CuH-Catalyzed fluorination of alkenes and PET applications

• Grant number: 17/26673-2
• Support Opportunities: Scholarships in Brazil - Post-Doctoral
• Start date: May 01, 2018
• End date: June 30, 2019
• Field of knowledge: Physical Sciences and Mathematics - Chemistry - Organic Chemistry
• Principal Investigator: Helio Alexandre Stefani
• Grantee: Carlos Henrique Alves Esteves
• Host Institution: Faculdade de Ciências Farmacêuticas (FCF). Universidade de São Paulo (USP). São Paulo , SP, Brazil
• Associated scholarship(s): 18/23115-1 - CuH-catalyzed hydrofluorination of aryl alkenes, BE.EP.PD

Abstract

Fluorinated organic compounds have a great impact in our society: 20% of the annualrevenue in the pharma industry comes from organofluorinated molecules and 30% of all newdrugs contain at least one fluorine atom. In the crop protection business, strategic for Brazil, a 25% share is reported.Similarly, the introduction of the isotope 18F revolutionized diagnostic medicine with PET(Positron Emission Tomography), especially in oncology and neuroscience; PET alsocontributes to the discovery of new drugs and the in vivo mapping of biological processes.This project proposes the development of a new synthetic methodology to forge C-F bondsin an enantioselective fashion from alkenes, an abundant and cheap chemical feedstock. Ourproposal is inspired by the CuH-catalyzed hydroamination reaction. The execution of this project could contribute to science in Brazil as currently no research group studies organofluorination in the country and, therefore, the study of new reactions for 18F incorporation in organic molecules also does not exist.

Scientific publications

(9)

(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)

DE OLIVEIRA, ISADORA M.; DARBEM, MARIANA P.; ESTEVES, C. HENRIQUE A.; PIMENTA, DANIEL C.; ZUKERMAN-SCHPECTOR, JULIO; STEFANI, HELIO A.; MANARIN, FLAVIA. Ytterbium-catalyzed formal [4+2] cycloaddition: Synthesis of chalcogen-quinolines 3-unsubstituted. Tetrahedron Letters, v. 59, n. 44, p. 3907-3911, OCT 31 2018. (16/04289-3, 17/26673-2, 16/24396-9)

DARBEM, MARIANA P.; KANNO, KARINA S.; DE OLIVEIRA, ISADORA M.; ESTEVES, C. HENRIQUE A.; PIMENTA, DANIEL C.; STEFANI, HELIO A.. Synthesis of amidoglucals and glucal esters via carbonylative coupling reactions of 2-iodoglucal using Mo(CO)(6) as a CO source. NEW JOURNAL OF CHEMISTRY, v. 43, n. 2, p. 696-699, JAN 14 2019. (17/26673-2, 17/24821-4, 16/04289-3, 16/24396-9)

DARBEM, MARIANA P.; ESTEVES, HENRIQUE A.; DE OLIVEIRA, ISADORA M.; PIMENTA, DANIEL C.; STEFANI, HELIO A.. Palladium-Catalyzed Thio- and Selenocarbonylation of 2-Iodoglycals. CHEMCATCHEM, v. 12, n. 2, NOV 2019. (16/24396-9, 16/04289-3, 17/26673-2, 17/24821-4)

DARBEM, MARIANA P.; ESTEVES, C. HENRIQUE A.; DE OLIVEIRA, ISADORA M.; REIS, JOEL S.; PIMENTA, DANIEL C.; STEFANI, HELIO A.. Synthesis of d-glyco-alkynone derivatives via carbonylative Sonogashira reaction. RSC ADVANCES, v. 9, n. 17, p. 9468-9474, 2019. (17/26673-2, 16/04289-3, 17/24821-4, 16/02392-1, 16/24396-9)

ESTEVES, HENRIQUE A.; DARBEM, MARIANA P.; PIMENTA, DANIEL C.; STEFANI, HELIO A.. Carbonylative Negishi-Type Coupling of 2-Iodoglycals with Alkyl and Aryl Halides. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, v. 2019, n. 44, p. 7384-7388, NOV 30 2019. (17/26673-2, 17/24821-4, 16/24396-9)

DE OLIVEIRA, ISADORA M.; ESTEVES, HENRIQUE A.; DARBEM, MARIANA P.; SARTORELLI, ARTHUR; CORRERA, THIAGO C.; RODRIGUES-OLIVEIRA, ANDRE F.; PIMENTA, DANIEL C.; ZUKERMAN-SCHPECTOR, JULIO; MANARIN, FLAVIA; STEFANI, HELIO A.. Stereo- and Regioselective Cu-Catalyzed Hydroboration of Alkynyl Chalcogenoethers. CHEMCATCHEM, v. 12, n. 13, MAY 2020. (16/04289-3, 14/50316-7, 17/24821-4, 16/24396-9, 17/26673-2)

DARBEM, MARIANA P.; ESTEVES, HENRIQUE A.; DE OLIVEIRA, ISADORA M.; STEFANI, HELIO A.. alpha,beta-Unsaturated 2-Ketoglycosides via Pd-Catalyzed Carbonylative Heck Reaction of 2-Iodoglycals. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, v. 2020, n. 32, JUL 2020. (16/24396-9, 16/04289-3, 17/26673-2, 14/50316-7, 17/24821-4)

DE OLIVEIRA, ISADORA M.; ESTEVES, C. HENRIQUE A.; DARBEM, MARIANA P.; PIMENTA, DANIEL C.; ZUKERMAN-SCHPECTOR, JULIO; FERREIRA, ANTONIO G.; STEFANI, HELIO A.; MANARIN, FLAVIA. Iron (III)-Promoted Synthesis of Substituted 4H-Chalcogenochromenes and Chemoselective Functionalization. ADVANCED SYNTHESIS & CATALYSIS, v. 361, n. 13, p. 3163-3172, JUL 2 2019. (17/26673-2, 17/24821-4, 16/04289-3, 16/24396-9)

BALFOUR, MICHAEL N.; ZUKERMAN-SCHPECTOR, JULIO; DAVILA RODRIGUEZ, MARIA JOSE; REIS, JOEL SAVI; ESTEVES, CARLOS HENRIQUE A.; STEFANI, HELIO A.. Combination of Sonogashira coupling and 5-endo-dig cyclization for the synthesis of 2,6-disubstituted-5-azaindoles. Synthetic Communications, v. 49, n. 3, p. 351-358, FEB 1 2019. (14/19221-0, 16/02392-1, 17/26673-2, 17/24821-4)