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

Rostoll-Berenguer, Jaume; Blay, Gonzalo; Pedro, José R.; Vila, Carlos

doi:10.3390/catal8120653

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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

Submission 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)

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Abstract

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.

Keywords: 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. https://doi.org/10.3390/catal8120653

AMA Style

Rostoll-Berenguer J, Blay G, Pedro JR, 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(12):653. https://doi.org/10.3390/catal8120653

Chicago/Turabian Style

Rostoll-Berenguer, Jaume, Gonzalo Blay, José R. Pedro, and Carlos Vila. 2018. "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 8, no. 12: 653. https://doi.org/10.3390/catal8120653

APA Style

Rostoll-Berenguer, J., Blay, G., Pedro, J. R., & Vila, C. (2018). 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, 8(12), 653. https://doi.org/10.3390/catal8120653

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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

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