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(Reference retrieved automatically from Web of Science through information on FAPESP grant and its corresponding number as mentioned in the publication by the authors.)

Metal-Free Photoinduced Hydroalkylation Cascade Enabled by an Electron-Donor-Acceptor Complex

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Author(s):
Correia, Jose Tiago M. [1] ; da Silva, Gustavo Piva [1] ; Kisukuri, Camila M. [1] ; Andre, Elias [1] ; Pires, Bruno [1] ; Carneiro, Pablo S. [1] ; Paixao, Marcio W. [1]
Total Authors: 7
Affiliation:
[1] Univ Fed Sao Carlos, Ctr Excellence Res Sustainable Chem CERSusChem, Dept Chem, BR-13565905 Sao Carlos, SP - Brazil
Total Affiliations: 1
Document type: Journal article
Source: Journal of Organic Chemistry; v. 85, n. 15, p. 9820-9834, AUG 7 2020.
Web of Science Citations: 0
Abstract

A metal- and photocatalyst-free photoinduced radical cascade hydroalkylation of 1,7-enynes has been disclosed. The process is triggered by a single electron transfer (SET) event involving a photoexcited electron-donor-acceptor complex between an NHPI ester and a Hantzsch ester, which decomposes to afford a tertiary radical that is readily trapped by the enyne. The method provides an operationally simple, robust, and step-economical approach toward the construction of diversely functionalized dihydroquinolinones bearing quaternary centers. A sequential one-pot hydroalkylation-isomerization approach is also offered, giving access to a family of quinolinones. A wide substrate scope and high functional group tolerance were observed in both approaches. (AU)

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: 15/17141-1 - Development and Mechanism Studies of New Synthetic Methodologies for the Synthesis of Bioactive Compounds.
Grantee:Ricardo Samuel Schwab
Support Opportunities: Regular Research Grants
FAPESP's process: 18/12986-1 - Development of photochemical and electrocatalytic methodologies to the synthesis and modification of heterocyclic scaffolds
Grantee:Camila de Menezes Kisukuri
Support Opportunities: Scholarships in Brazil - Post-Doctoral
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