Preprint Article Version 1 This version is not peer-reviewed

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

Version 1 : Received: 12 November 2018 / Approved: 15 November 2018 / Online: 15 November 2018 (05:15:56 CET)

A peer-reviewed article of this Preprint also exists.

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. 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.

Journal reference: Catalysts 2018, 8, 653
DOI: 10.3390/catal8120653

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 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.

Subject Areas

visible-light photocatalysis; organophotoredox catalysis; friedel-crafts reaction; indoles; 1,4-benzoxazin-2-ones

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