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Arylation reactions of heterocycles photocatalysed by porphyrins in both batch and continuous flow conditions

Grant number: 18/00879-6
Support type:Scholarships in Brazil - Doctorate
Effective date (Start): April 01, 2018
Effective date (End): March 31, 2021
Field of knowledge:Physical Sciences and Mathematics - Chemistry
Principal Investigator:Kleber Thiago de Oliveira
Grantee:Rodrigo Costa e Silva
Home Institution: Centro de Ciências Exatas e de Tecnologia (CCET). Universidade Federal de São Carlos (UFSCAR). São Carlos , SP, Brazil

Abstract

In this project, photocatalyzed arylation reactions of heterocyclic derivatives will be studied by using porphyrins as photocatalysts. The reactions will be explored in both batch and continuous flow conditions. Our main objective is to develop an improved methodology allowing the scale up in C(sp2)-H functionalization reactions by the use of porphyrin derivatives as photocatalysts (Single Electron Transfer -SET), and aryl-diazonium salts as source of aryl radicals. Diazine derivatives such as pyrimidines, pyrazines and pyridazines were selected as targets, allowing the application of the methodology for the synthesis APIs (active pharmaceutical ingredients) or drug candidates.The development of protocols under continuous flow conditions will be essential in this work, as it should bring safety, scaling up and photocatalytic efficiency to the studies as a whole. It is important to highlight the positive differentials that the continuous reactors have delivered when developed and applied in photo-processes in the literature and industry.

Scientific publications
(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)
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. Web of Science Citations: 0.
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. Web of Science Citations: 1.

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