Photocatalyzed Reactions by using porphyrins and continuous flow conditions: Arylations of heterocycles and activated olefins.

• Grant number: 18/00106-7
• Support Opportunities: Regular Research Grants
• Start date: April 01, 2018
• End date: March 31, 2020
• Field of knowledge: Physical Sciences and Mathematics - Chemistry - Organic Chemistry
• Principal Investigator: Kleber Thiago de Oliveira
• Grantee: Kleber Thiago de Oliveira
• Host Institution: Centro de Ciências Exatas e de Tecnologia (CCET). Universidade Federal de São Carlos (UFSCAR). São Carlos , SP, Brazil
• Associated scholarship(s): 18/14837-3 - Photocatalyzed reactions by using porphyrins and continuous flow conditions: arylations of heterocycles and activated olefins, BP.TT

Abstract

Herein, photocatalyzed reactions in batch and under continuous flow conditions will be studied by using porphyrin derivatives as photosensitizers (Figure i). Our aims are to advance in the state of art of photocatalyzed processes mediated by porphyrins developing arylation reactions of electrons rich olefins, O-heteroarenes and N-heteroarenes. Particularly, diazonium salts will be used as radical source, which will be generated by photocatalysis (SET). In general, in this project we propose to develop a direct photoarylation methodology with potential applications in natural product synthesis and APIs preparations. (AU)

Scientific publications

(22)

(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 SOUZA, JULIANA M.; ABDIAJ, IRINI; CHEN, JIAQI; HANSON, KENNETH; DE OLIVEIRA, KLEBER T.; MCQUADE, D. TYLER. Increasing Scope of Clickable Fluorophores: Electrophilic Substitution of Ylidenemalononitriles. Journal of Organic Chemistry, v. 85, n. 18, p. 11822-11834, SEP 18 2020. (18/14555-8, 18/00106-7)

DE SOUZA, JULIANA M.; BROCKSOM, TIMOTHY J.; MCQUADE, D. TYLER; DE OLIVEIRA, KLEBER T.. Continuous Endoperoxidation of Conjugated Dienes and Subsequent Rearrangements Leading to C-H Oxidized Synthons. Journal of Organic Chemistry, v. 83, n. 15, p. 7574-7585, AUG 3 2018. (11/13993-2, 13/07276-1, 18/00106-7, 15/21110-4)

BARTOLOMEU, ALOISIO DE A.; SILVA, RODRIGO C.; BROCKSOM, TIMOTHY J.; NOEL, TIMOTHY; DE OLIVEIRA, KLEBER T.. Photoarylation of Pyridines Using Aryldiazonium Salts and Visible Light: An EDA Approach. Journal of Organic Chemistry, v. 84, n. 16, p. 10459-10471, AUG 16 2019. (13/07276-1, 18/00106-7, 14/24506-3, 18/08772-6, 18/00879-6)

DE SOUZA, LARISSA MARILA; INADA, NATALIA MAYUMI; VENTURINI, FRANCINE PERRI; CARMONA-VARGAS, CHRISTIAN C.; PRATAVIEIRA, SEBASTIAO; DE OLIVEIRA, KLEBER THIAGO; KURACHI, CRISTINA; BAGNATO, VANDERLEI SALVADOR. Photolarvicidal effect of curcuminoids from Curcuma longa Linn. against Aedes aegypti larvae. JOURNAL OF ASIA-PACIFIC ENTOMOLOGY, v. 22, n. 1, p. 151-158, MAR 2019. (09/54035-4, 13/07276-1, 18/00106-7)

LEITE, TAISE H. O.; GRAWE, GREGORY; HONORATO, JOAO; CUNHA, BEATRIZ N.; NASCIMENTO, OTACIRO R.; DE VARGAS, PAMELA S.; DONATONI, CAROLINA; OLIYEIRA, KLEBER T.; LOPES, JEFFERSON M. S.; BARBOSA NETO, NEWTON M.; et al. Remarkable Electronic Effect on the meso-Tetra(thienyl)porphyrins. Inorganic Chemistry, v. 58, n. 2, p. 1030-1039, JAN 21 2019. (18/00106-7, 15/21110-4, 16/16312-0)

DA SILVA GOBO, NICHOLAS ROBERTO; BROCKSOM, TIMOTHY JOHN; DE OLIVEIRA, KLEBER THIAGO. Synthesis of a Naphthalocyanine-Like Dye: The First Report on Zn(II)-1,6-methano[10]annulenecyanine. Molecules, v. 25, n. 9, MAY 2020. (18/00106-7, 13/07276-1, 12/24092-9)

RODRIGUES, FABIO M. S.; TAVARES, IURI; AROSO, RAFAEL T.; DIAS, LUCAS D.; DOMINGOS, CAROLINA V.; DE FARIA, CLARA M. G.; PICCIRILLO, GIUSI; MARIA, TERESA M. R.; CARRILHO, RUI M. B.; BAGNATO, VANDERLEI S.; et al. Photoantibacterial Poly(vinyl)chloride Films Applying Curcumin Derivatives as Bio-Based Plasticizers and Photosensitizers. Molecules, v. 28, n. 5, p. 16-pg., 2023-03-01. (18/00106-7, 19/13569-8, 13/07276-1, 14/50857-8)

SAMPAIO, LAIS SIMOES; DE ANNUNZIO, SARAH RAQUEL; DE FREITAS, LAURA MARISE; DANTAS, LIVIA OLIVEIRA; DE BONI, LEONARDO; DONATONI, MARIA CAROLINA; DE OLIVEIRA, KLEBER THIAGO; FONTANA, CARLA RAQUEL. Influence of light intensity and irradiation mode on methylene blue, chlorin-e6 and curcumin-mediated photodynamic therapy against Enterococcus faecalis. Photodiagnosis and Photodynamic Therapy, v. 31, p. 13-pg., 2020-09-01. (18/23015-7, 18/00106-7, 13/07276-1, 18/09088-1)

DE SOUZA, LARISSA MARILA; VENTURINI, FRANCINE PERRI; INADA, NATALIA MAYUMI; IERMAK, IEVGENIIA; GARBUIO, MATHEUS; MEZZACAPPO, NATASHA FERREIRA; DE OLIVEIRA, KLEBER THIAGO; BAGNATO, VANDERLEI SALVADOR. Curcumin in formulations against Aedes aegypti: Mode of action, photolarvicidal and ovicidal activity. Photodiagnosis and Photodynamic Therapy, v. 31, p. 12-pg., 2020-09-01. (18/00106-7, 09/54035-4, 13/07276-1)

RAMOS, LUIZ D.; DE MACEDO, LEONARDO H.; GOBO, NICHOLAS R. S.; DE OLIVEIRA, KLEBER T.; CERCHIARO, GISELLE; MORELLI FRIN, KARINA P.. Understanding the photophysical properties of rhenium(I) compounds coordinated to 4,7-diamine-1,10-phenanthroline: synthetic, luminescence and biological studies. DALTON TRANSACTIONS, v. 49, n. 45, p. 16154-16165, DEC 7 2020. (18/14152-0, 18/00106-7, 17/18063-0, 16/09652-9)

COSTA E SILVA, RODRIGO; DA SILVA, LUELY OLIVEIRA; BARTOLOMEU, ALOISIO DE ANDRADE; BROCKSOM, TIMOTHY JOHN; DE OLIVEIRA, KLEBER THIAGO. Recent applications of porphyrins as photocatalysts in organic synthesis: batch and continuous flow approaches. Beilstein Journal of Organic Chemistry, v. 16, p. 917-955, MAY 6 2020. (18/00106-7, 18/00879-6, 14/24506-3)

MUELLER, ANDRESSA V.; DE OLIVEIRA, KLEBER T.; MEYER, GERALD J.; POLO, ANDRE S.. Inhibiting Charge Recombination in cis-Ru(NCS)(2) Diimine Sensitizers with Aromatic Substituents. ACS APPLIED MATERIALS & INTERFACES, v. 11, n. 46, p. 43223-43234, NOV 20 2019. (18/08038-0, 18/00106-7, 16/24020-9, 16/21993-6)

SILVA, TAYNARA L.; BARTOLOMEU, ALOISIO DE A.; DE JESUS, HUGO C. R.; DE OLIVEIRA, KLEBER T.; FERNANDES, JOAO B.; BROMME, DIETER; VIEIRA, PAULO C.. New Synthetic Quinolines as Cathepsin K Inhibitors. Journal of the Brazilian Chemical Society, v. 31, n. 8, p. 1605-1613, AUG 2020. (17/15455-4, 14/24506-3, 18/00106-7, 12/11819-8)

BATISTA, GABRIEL M. F.; DE CASTRO, PEDRO P.; DOS SANTOS, HELIO F.; DE OLIVEIRA, KLEBER T.; AMARANTE, GIOVANNI W.. Electron-Donor-Acceptor Complex-Enabled Flow Methodology for the Hydrotrifluoromethylation of Unsaturated beta-Keto Esters. ORGANIC LETTERS, v. 22, n. 21, p. 8598-8602, NOV 6 2020. (13/07276-1, 18/00106-7)

VENTURINI, FRANCINE PERRI; DE SOUZA, LARISSA MARILA; GARBUIO, MATHEUS; INADA, NATALIA MAYUMI; DE SOUZA, JAQUELINE PEROLA; KURACHI, CRISTINA; DE OLIVEIRA, KLEBER THIAGO; BAGNATO, VANDERLEI SALVADOR. Environmental safety and mode of action of a novel curcumin-based photolarvicide. Environmental Science and Pollution Research, v. 27, n. 23, MAY 2020. (18/00106-7, 13/07276-1)

DE SOUZA, ALINE A. N.; SILVA, NATHALIA S.; MUELLER, ANDRESSA V.; POLO, ANDRE S.; BROCKSOM, TIMOTHY J.; DE OLIVEIRA, KLEBER T.. Porphyrins as Photoredox Catalysts in Csp(2)-H Arylations: Batch and Continuous Flow Approaches. Journal of Organic Chemistry, v. 83, n. 24, p. 15077-15086, DEC 21 2018. (15/21110-4, 13/07276-1, 18/00106-7, 16/24020-9, 16/21993-6)

SILVA, RODRIGO C.; VILLELA, LUCAS F.; BROCKSOM, TIMOTHY J.; DE OLIVEIRA, KLEBER T.. Direct C-H photoarylation of diazines using aryldiazonium salts and visible-light. RSC ADVANCES, v. 10, n. 52, p. 8-pg., 2020-08-25. (18/00106-7, 18/00879-6, 13/07276-1)

DE SOUZA, JULIANA M.; ABDIAJ, IRINI; CHEN, JIAQI; HANSON, KENNETH; DE OLIVEIRA, KLEBER T.; MCQUADE, D. TYLER. Synthesis of multi-substituted pyridines from ylidenemalononitriles and their emission properties. ORGANIC & BIOMOLECULAR CHEMISTRY, v. 19, n. 9, p. 1991-1999, MAR 7 2021. (18/14555-8, 18/00106-7)

DIAS, LUCAS D.; ALVES, FERNANDA; BUZZA, HILDE H.; BAGNATO, VANDERLEI S.. Photodisinfection of material surfaces and bacterial skin infections by a detergent loaded with curcumin. Photodiagnosis and Photodynamic Therapy, v. 39, p. 7-pg., 2022-09-01. (18/00106-7, 19/13569-8, 14/50857-8, 21/01324-0, 13/07276-1)

DIAS, LUCAS D.; CARBINATTO, FERNANDA MANSANO; ALMEIDA, ISABELLE DA SILVEIRA; BLANCO, KATE C.; MARQUELE-OLIVEIRA, FRANCIANE; MUNARI, CARLA CAROLINA; BAGNATO, VANDERLEI SALVADOR. Eco-Friendly Extraction of Green Coffee Oil for Industrial Applications: Its Antioxidant, Cytotoxic, Clonogenic, and Wound Healing Properties. FERMENTATION-BASEL, v. 9, n. 4, p. 13-pg., 2023-04-01. (18/00106-7, 19/13569-8, 13/07276-1, 14/50857-8)

LINARES, IRWIN A. P.; VELASQUEZ, ANGELA M. A.; GRAMINHA, MARCIA A. S.; DE OLIVEIRA, KLEBER T.; PERUSSI, JANICE RODRIGUES. Antileishmanial activity of amphiphilic chlorin derivatives mediated by photodynamic therapy. Photodiagnosis and Photodynamic Therapy, v. 31, p. 9-pg., 2020-09-01. (18/00106-7, 17/03552-5, 13/07276-1, 19/21661-1)

NIE, MIN; DENG, DONG MEI; WU, YAFEI; DE OLIVEIRA, KLEBER THIAGO; BAGNATO, VANDERLEI SALVADOR; CRIELAARD, WIM; RASTELLI, ALESSANDRA NARA DE SOUZA. Photodynamic inactivation mediated by methylene blue or chlorin e6 against Streptococcus mutans biofilm. Photodiagnosis and Photodynamic Therapy, v. 31, p. 7-pg., 2020-09-01. (15/21183-1, 13/07276-1, 18/00106-7)