Organophotocatalytic Intramolecular Formal Enyne-Metathesis - An Alternative to Transition-Metal Catalysis

Author(s)

Souza, Wanderson C. ; Correia, Jose Tiago M. ; Matos, Priscilla M. ; Kisukuri, Camila M. ; Carneiro, Pablo S. ; Paixao, Marcio W.

• Document type: Journal article
• Source: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY; v. 2022, n. 16, p. 5-pg., 2022-02-05.

Abstract

A new approach to access 1,3-diene derived quinolinone compounds has been realized using a mild reaction protocol employing a metal free catalyst (1,2,3,5-tetrakis(carbazol-9-yl)-4,6-dicyanobenzene) (4CzIPN), blue LED as activation source, and benefits from a sustainable solvent dimethylcarbonate (DMC). The mechanism is postulated as an amide-tethered enyne intramolecular [2+2]-photocatalyzed cycloaddition-retrocycloaddition sequence, proceeding via a cyclobutene intermediate species. The methodology offers an efficient route towards decorated 1,3-diene products. (AU)

• FAPESP's process: 21/06099-5 - Development of new photochemical methodologies for the synthesis of small molecule and biomolecule modifications
• Grantee: Márcio Weber Paixão
• Support Opportunities: Regular Research Grants
• FAPESP's process: 17/10015-6 - Photocatalysis Applied to the Synthesis of N-heterocycles: New Strategies for Intercepting Radical Intermediates Generated in Processes Promoted by Visible-light-Tris (trimethylsilyl)silane Combination.
• Grantee: José Tiago Menezes Correia
• Support Opportunities: Scholarships in Brazil - Post-Doctoral
• FAPESP's process: 14/50249-8 - Green chemistry: sustainable synthetic methods employing benign solvents, safer reagents, and bio-renewable feedstock
• Grantee: Arlene Gonçalves Corrêa
• Support Opportunities: Research Grants - Research Centers in Engineering Program
• FAPESP's process: 20/00556-2 - Investigation of S-C bond formation using photochemistry
• Grantee: Priscilla Mendonça Matos
• Support Opportunities: Scholarships in Brazil - Post-Doctoral