Photochemical ?-Aminonitrile Synthesis Using Zn-Phthalocyaninesas Near-Infrared Photocatalysts

Author(s)

Grundke, Caroline ; Silva, Rodrigo C. ; Kitzmann, Winald R. ; Heinze, Katja ; de Oliveira, Kleber T. ; Opatz, Till

• Document type: Journal article
• Source: Journal of Organic Chemistry; v. 87, n. 9, p. 13-pg., 2022-05-06.

Abstract

While photochemical transformations with sunlight almostexclusively utilize the UV-vis part of the solar spectrum, the majority ofthe photons emitted by the sun have frequencies in the near-infraredregion. Phthalocyanines show high structural similarity to the naturallyoccurring light-harvesting porphyrins, chlorins, and mainly bacteriochlor-ins and are also known for being efficient and affordable near-infrared lightabsorbers as well as triplet sensitizers for the production of singlet oxygen.Although having been neglected for a long time in synthetic organicchemistry due to their low solubility and high tendency towardaggregation, their unique photophysical properties and chemical robust-ness make phthalocyanines attractive photocatalysts for the application innear-infrared-light-driven synthesis strategies. Herein, we report a cheap,simple, and efficient photocatalytic protocol, which is easily scalable undercontinuous-flow conditions. Various phthalocyanines were studied as near-infrared photosensitizers in oxidative cyanations oftertiary amines to generate alpha-aminonitriles, a synthetically versatile compound class (AU)

• FAPESP's process: 18/00879-6 - Arylation reactions of heterocycles photocatalysed by porphyrins in both batch and continuous flow conditions.
• Grantee: Rodrigo Costa e Silva
• Support Opportunities: Scholarships in Brazil - Doctorate
• FAPESP's process: 20/06874-6 - Applications of technologies and synthetic methodologies developed under continuous flow conditions at LQBO-UFSCar for the preparation of molecules with biological activities and APIs
• Grantee: Kleber Thiago de Oliveira
• Support Opportunities: Regular Research Grants
• FAPESP's process: 19/27176-8 - Asymmetric photocatalysis applied to the synthesis of Brivaracetam: synthetic approaches employing enabling technologies for chemical synthesis
• Grantee: Kleber Thiago de Oliveira
• Support Opportunities: Regular Research Grants