Photochemical reactions applied to the synthesis of substituted indoles via radical insertion reactions to isonitriles

• Grant number: 17/03120-8
• Support Opportunities: Scholarships in Brazil - Post-Doctoral
• Start date: May 01, 2017
• End date: December 31, 2019
• Field of knowledge: Physical Sciences and Mathematics - Chemistry - Organic Chemistry
• Agreement: GlaxoSmithKline
• Principal Investigator: Arlene Gonçalves Corrêa
• Grantee: Marília Simão dos Santos
• Host Institution: Centro de Ciências Exatas e de Tecnologia (CCET). Universidade Federal de São Carlos (UFSCAR). São Carlos , SP, Brazil
• Associated research grant: 14/50249-8 - Green chemistry: sustainable synthetic methods employing benign solvents, safer reagents, and bio-renewable feedstock, AP.PCPE
• Associated scholarship(s): 18/20956-5 - C-H Functionalization of Aliphatic and Aromatic Heterocycles by Visible Light Photoredox Catalysis, BE.EP.PD

Abstract

Chemistry and industry development has enabled modifications in raw materials, as well as the creation of new materials, which facilitate and accompany the modernization of the society's lifestyle. However, the progress has been achieved associate with the increase of non-renewable resources use and waste generation, rising concern on environmental issues. In this context, the green chemistry term was introduced - area which is concerned with the development of products, technologies and processes to prevent the generation of pollution. Thus, the sustainability concept arose from the need to create environmental friendly processes from both academy and industry, considering the continuous economic and social development. In this way, photocatalysis has attracted worldwide attention due to the ability to convert solar energy into chemical energy by a wide range of applications. Among them, development of methodologies focused on the synthesis of compounds with chemical and biological relevance. Therefore, this research project aims to explore photochemical reactions promoted by visible light through photoredox catalysis mediated by transition metals and photo-organocatalysts. Effectively, new methodologies for the synthesis of substituted indole will be investigated through radical cascade reactions using isocyanates. Inicially, the reactions will be performed in batch mode, and after in a continuous flow mode. The continuous flow technology will be evaluated in the synthesis of an indomethacin drug analogue, an anti-inflammatory drug. (AU)

Scientific publications

(4)

(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)

SANTOS, MARILIA S.; CORREA, ARLENE G.; PAIXAO, MARCIO W.; KOENIG, BURKHARD. C(sp(3))-C(sp(3)) Cross-Coupling of Alkyl Bromides and Ethers Mediated by Metal and Visible Light Photoredox Catalysis. ADVANCED SYNTHESIS & CATALYSIS, v. 362, n. 12, APR 2020. (14/50249-8, 18/20956-5, 17/03120-8)

PAIXAO, MARCIO W.. Photoredox Catalysis toward 2-Sulfenylindole Synthesis through a Radical Cascade Process. ORGANIC LETTERS, v. 22, n. 11, p. 4266-4271, JUN 5 2020. (14/50249-8, 17/03120-8, 18/12986-1, 15/17141-1)

CORREIA, JOSE TIAGO M.; SANTOS, MARILIA S.; PISSINATI, EMANUELE F.; DA SILVA, GUSTAVO P.; PAIXAO, MARCIO W.. Recent Advances on Photoinduced Cascade Strategies for the Synthesis of N-Heterocycles. CHEMICAL RECORD, v. 21, n. 10, SI, JUL 2021. (17/10015-6, 14/50249-8, 17/03120-8)

DANTAS, JULIANA A.; ECHEMENDIA, RADELL; SANTOS, MARILIA S.; PAIXAO, MARCIO W.; FERREIRA, MARCO ANTONIO B.; CORREA, ARLENE G.. Green Approach for Visible-Light-Induced Direct Functionalization of 2-Methylquinolines. Journal of Organic Chemistry, v. 85, n. 18, p. 16-pg., 2020-09-18. (13/07600-3, 20/01255-6, 15/08541-6, 14/50249-8, 17/03120-8)