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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.)

Photocatalyzed Intramolecular [2+2] Cycloaddition of N-Alkyl-N-(2-(1-arylvinyl)aryl)cinnamamides

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Author(s):
de Souza, Wanderson C. [1] ; Matsuo, Bianca T. [1] ; Matos, Priscilla M. [1] ; Correia, Jose Tiago M. [1] ; Santos, Marilia S. [2, 1] ; Koenig, Burkhard [2] ; Paixao, Marcio W. [1]
Total Authors: 7
Affiliation:
[1] Fed Univ Sao Carlos UFSCar, Ctr Excellence Res Sustainable Chem, Dept Chem, CERSusChem, Sao Carlos, SP - Brazil
[2] Univ Regensburg, Inst Organ Chem, Univ Str 31, D-93053 Regensburg - Germany
Total Affiliations: 2
Document type: Journal article
Source: CHEMISTRY-A EUROPEAN JOURNAL; v. 27, n. 11 JAN 2021.
Web of Science Citations: 0
Abstract

N-Alkyl-N-(2-(1-arylvinyl)aryl)cinnamamides are converted into natural product inspired scaffolds via iridium photocatalyzed intramolecular {[}2+2] photocycloaddition. The protocol has a broad substrate scope, whilst operating under mild reaction conditions. Tethering four components forming a trisubstituted cyclobutane core builds rapidly high molecular complexity. Our approach allows the design and synthesis of a variety of tetrahydrocyclobuta{[}c]quinolin-3(1H)-ones, in yields ranging between 20-99 %, and with excellent regio- and diastereoselectivity. Moreover, it was demonstrated that the intramolecular {[}2+2]-cycloaddition of 1,7-enynes-after fragmentation of the cyclobutane ring-leads to enyne-metathesis-like products. (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: 20/00556-2 - Investigation of S-C bond formation using photochemistry
Grantee:Priscilla Mendonça Matos
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