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Open AccessArticle

9,10-Phenanthrenedione as Visible-Light Photoredox Catalyst: A Green Methodology for the Functionalization of 3,4-Dihydro-1,4-Benzoxazin-2-Ones through a Friedel-Crafts Reaction

Departament de Química Orgànica, Facultat de Química, Universitat de València, Dr. Moliner 50, 46100 Burjassot, València, Spain
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Catalysts 2018, 8(12), 653; https://doi.org/10.3390/catal8120653
Received: 12 November 2018 / Revised: 1 December 2018 / Accepted: 6 December 2018 / Published: 12 December 2018
(This article belongs to the Special Issue Photocatalytic Organic Synthesis)
A visible-light photoredox functionalization of 3,4-dihydro-1,4-benzoxazin-2-ones through a Friedel-Crafts reaction with indoles using an inexpensive organophotoredox catalyst is described. The reaction uses a dual catalytic system that is formed by a photocatalyst simple and cheap, 9,10-phenanthrenedione, and a Lewis acid, Zn(OTf)2. 5W white LEDs are used as visible-light source and oxygen from air as a terminal oxidant, obtaining the corresponding products with good yields. The reaction can be extended to other electron-rich arenes. Our methodology represents one of the most valuable and sustainable approach for the functionalization of 3,4-dihydro-1,4-benzoxazin-2-ones, as compared to the reported procedures. Furthermore, several transformations were carried out, such as the synthesis of the natural product cephalandole A and a tryptophol derivative. View Full-Text
Keywords: visible-light photocatalysis; organophotoredox catalysis; Friedel-Crafts reaction; indoles; 1,4-benzoxazin-2-ones visible-light photocatalysis; organophotoredox catalysis; Friedel-Crafts reaction; indoles; 1,4-benzoxazin-2-ones
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MDPI and ACS Style

Rostoll-Berenguer, J.; Blay, G.; Pedro, J.R.; Vila, C. 9,10-Phenanthrenedione as Visible-Light Photoredox Catalyst: A Green Methodology for the Functionalization of 3,4-Dihydro-1,4-Benzoxazin-2-Ones through a Friedel-Crafts Reaction. Catalysts 2018, 8, 653.

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